CA1230594A - N-glycosylated carboxamide derivatives, process for their preparation and their use for influencing the body's inherent defences - Google Patents
N-glycosylated carboxamide derivatives, process for their preparation and their use for influencing the body's inherent defencesInfo
- Publication number
- CA1230594A CA1230594A CA000425694A CA425694A CA1230594A CA 1230594 A CA1230594 A CA 1230594A CA 000425694 A CA000425694 A CA 000425694A CA 425694 A CA425694 A CA 425694A CA 1230594 A CA1230594 A CA 1230594A
- Authority
- CA
- Canada
- Prior art keywords
- glucopyranosyl
- octadecyl
- deoxy
- process according
- group
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title abstract description 33
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- -1 glycosyl radical Chemical class 0.000 claims description 97
- 239000002253 acid Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 claims description 14
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 claims description 9
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 8
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 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 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UNSKAUSCLTVFGO-FSIIMWSLSA-N methyl (2s,3s,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexanoate Chemical compound COC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O UNSKAUSCLTVFGO-FSIIMWSLSA-N 0.000 claims description 4
- 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 claims description 4
- HDZVAKYKVBEOFL-MLYSRARTSA-N (2r,3s,4s,5r)-2-(hydroxymethyl)-6-(octadecylamino)oxane-3,4,5-triol Chemical compound CCCCCCCCCCCCCCCCCCNC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HDZVAKYKVBEOFL-MLYSRARTSA-N 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 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- VOIFKEWOFUNPBN-QIUUJYRFSA-N beta-D-glucuronamide Chemical compound NC(=O)[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O VOIFKEWOFUNPBN-QIUUJYRFSA-N 0.000 claims description 3
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 3
- 125000005640 glucopyranosyl group Chemical group 0.000 claims description 3
- 229950004542 glucuronamide Drugs 0.000 claims description 3
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- KFEUJDWYNGMDBV-LODBTCKLSA-N N-acetyllactosamine Chemical group O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KFEUJDWYNGMDBV-LODBTCKLSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 claims 3
- CGRNGAJCQIWCRM-CHVQCXDUSA-N (3r,4s,5r,6r)-2-(dodecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCCCCCCCNC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O CGRNGAJCQIWCRM-CHVQCXDUSA-N 0.000 claims 2
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical group [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims 2
- 125000000400 lauroyl group Chemical group O=C([*])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 claims 2
- WFMKUKPIVUIKTE-SCSBQZQXSA-N n-dodecyl-n-[(3r,4s,5r,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-SCSBQZQXSA-N 0.000 claims 2
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 101150111293 cor-1 gene Proteins 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 claims 1
- 125000003696 stearoyl group Chemical group O=C([*])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 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 230000001965 increasing effect Effects 0.000 abstract description 6
- 210000000987 immune system Anatomy 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 230000007123 defense Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- 235000000346 sugar Nutrition 0.000 description 23
- 241001465754 Metazoa Species 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 229930182474 N-glycoside Natural products 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 150000002341 glycosylamines Chemical class 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000006188 syrup Substances 0.000 description 12
- 235000020357 syrup Nutrition 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000011081 inoculation Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 150000001408 amides Chemical group 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000008163 sugars Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000007912 intraperitoneal administration Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 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 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 230000006181 N-acylation Effects 0.000 description 5
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 description 5
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- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229960005456 sisomicin Drugs 0.000 description 5
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- 239000011343 solid material Substances 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
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- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
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- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
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- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
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- UREJYVIZZWPATM-JOQFYAFYSA-N n-octadecyl-n-[(3s,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-JOQFYAFYSA-N 0.000 description 1
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- 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
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
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- 125000002948 undecyl 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])[H] 0.000 description 1
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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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3213650.1 | 1982-04-14 | ||
| 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 |
|---|---|
| CA1230594A true CA1230594A (en) | 1987-12-22 |
Family
ID=6160842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000425694A Expired 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 |
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) |
Families Citing this family (26)
| 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. |
| AU7613694A (en) * | 1993-08-30 | 1995-03-22 | Bayer Aktiengesellschaft | Glycosyl amides of 6-amino-6-deoxy sugars |
| DE4329094A1 (de) * | 1993-08-30 | 1995-03-02 | Bayer Ag | (Glycosylamid)-uronsäure-derivate |
| DK0716658T3 (da) * | 1993-08-30 | 1997-12-22 | Bayer Ag | Glycosylamider af 2-aminocylamino-2-desoxysukkerarter |
| 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 |
| PL1991266T3 (pl) | 2006-01-26 | 2013-11-29 | Zoetis Services Llc | Nowe kompozycje adiuwantów glikolipidowych |
Family Cites Families (6)
| 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
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 |
| NO831163L (no) | 1983-10-17 |
| IE55112B1 (en) | 1990-06-06 |
| DE3213650A1 (de) | 1983-10-27 |
| GR78512B (enExample) | 1984-09-27 |
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