JP4070966B2 - 新規ガラクトシルセラミド類縁体及び用途 - Google Patents
新規ガラクトシルセラミド類縁体及び用途 Download PDFInfo
- Publication number
- JP4070966B2 JP4070966B2 JP2001196016A JP2001196016A JP4070966B2 JP 4070966 B2 JP4070966 B2 JP 4070966B2 JP 2001196016 A JP2001196016 A JP 2001196016A JP 2001196016 A JP2001196016 A JP 2001196016A JP 4070966 B2 JP4070966 B2 JP 4070966B2
- Authority
- JP
- Japan
- Prior art keywords
- added
- ethyl
- skin
- glucocerebrosidase
- galactosylceramide
- 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
- 150000002254 galactosylceramides Chemical class 0.000 title claims description 17
- 102000004547 Glucosylceramidase Human genes 0.000 claims description 24
- 108010017544 Glucosylceramidase Proteins 0.000 claims description 24
- 239000012190 activator Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 210000003491 skin Anatomy 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- -1 benzyloxycarbonylamino Chemical group 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 210000000434 stratum corneum Anatomy 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000012156 elution solvent Substances 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 5
- 229940106189 ceramide Drugs 0.000 description 5
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 5
- 210000001339 epidermal cell Anatomy 0.000 description 5
- 210000002615 epidermis Anatomy 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 5
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- DJIPOPBSZYJSKL-OXZAUESDSA-N N-[1-(hexylamino)-1-oxo-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(C(=O)NCCCCCC)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O DJIPOPBSZYJSKL-OXZAUESDSA-N 0.000 description 4
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000002305 glucosylceramides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HRTYFECXABFHQW-MMXJFWRNSA-N N-[2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O HRTYFECXABFHQW-MMXJFWRNSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- POQRWMRXUOPCLD-HIIAJUEOSA-N beta-D-galactosyl-N-(tetracosanoyl)sphingosine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O POQRWMRXUOPCLD-HIIAJUEOSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- 239000003814 drug Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 210000002510 keratinocyte Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- GZEPUMKQABVKAO-UUKFOVPRSA-N n-[1-oxo-1-(tetradecylamino)-3-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropan-2-yl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(C(=O)NCCCCCCCCCCCCCC)CS[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O GZEPUMKQABVKAO-UUKFOVPRSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 3
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 208000015872 Gaucher disease Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- MAJZGYHXOPKSTC-RGFLIBBCSA-N N-[2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCS[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O MAJZGYHXOPKSTC-RGFLIBBCSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HECCELTVWFSACN-JIHNSMNRSA-N [(2r,3s,4s,5r,6s)-3,4,5-tribenzoyloxy-6-[2-(phenylmethoxycarbonylamino)ethylsulfanyl]oxan-2-yl]methyl benzoate Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](OC(=O)C=2C=CC=CC=2)[C@H]1OC(=O)C=1C=CC=CC=1)OC(=O)C=1C=CC=CC=1)SCCNC(=O)OCC=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 HECCELTVWFSACN-JIHNSMNRSA-N 0.000 description 2
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- 150000001783 ceramides Chemical class 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000006003 cornification Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
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- 230000037336 dry skin Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000005175 epidermal keratinocyte Anatomy 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
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- 239000006260 foam Substances 0.000 description 1
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- 239000003102 growth factor Substances 0.000 description 1
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- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUSDOSNQPDKDSQ-JJXLTNITSA-N methyl 2-(octadecanoylamino)-3-[(2s,3r,4s,5s,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(C(=O)OC)CS[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUSDOSNQPDKDSQ-JJXLTNITSA-N 0.000 description 1
- FEADQZMKQOMOMD-UHFFFAOYSA-N methyl 2-(phenylmethoxycarbonylamino)-3-sulfanylpropanoate Chemical compound COC(=O)C(CS)NC(=O)OCC1=CC=CC=C1 FEADQZMKQOMOMD-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
Images
Classifications
-
- 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
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001196016A JP4070966B2 (ja) | 2001-06-28 | 2001-06-28 | 新規ガラクトシルセラミド類縁体及び用途 |
| TW091114141A TWI322151B (enExample) | 2001-06-28 | 2002-06-27 | |
| US10/482,110 US7183261B2 (en) | 2001-06-28 | 2002-06-27 | Galactosylceramide analogs, and β-glucocerebrosidase activators, external skin preparations and method of activating β-glucocerebrosidase using the analogs |
| HK05100756.9A HK1067642B (en) | 2001-06-28 | 2002-06-27 | NOVEL GALACTOSYLCERAMIDE ANALOGS AND β - GLUCOCEREBROSIDASE ACTIVATORS, EXTERNAL SKIN PREPARATIONS AND METHOD OF ACTIVATING β-GLUCOCEREBROSIDASE USING THE ANALOGS |
| KR1020037016943A KR100739250B1 (ko) | 2001-06-28 | 2002-06-27 | 신규 갈락토실세라미드 유사체, 이를 사용한β-글루코세레브로시다제 활성화제, 피부 외용제 및β-글루코세레브로시다제 활성화 방법 |
| TW098132688A TW201002734A (en) | 2001-06-28 | 2002-06-27 | A ameliorating preparation for rough skin |
| PCT/JP2002/006532 WO2003002584A1 (en) | 2001-06-28 | 2002-06-27 | NOVEL GALACTOSYLCERAMIDE ANALOGS AND β-GLUCOCEREBROSIDASE ACTIVATORS, EXTERNAL SKIN PREPARATIONS AND METHOD OF ACTIVATING β-GLUCOCEREBROSIDASE USING THE ANALOGS |
| DE60232449T DE60232449D1 (de) | 2001-06-28 | 2002-06-27 | Neue galactosylceramidanaloga und beta-glucocerebrosidaseaktivatoren, zubereitungen für die äusserliche anwendung auf der haut und verfahren zur aktivierung von beta-glucocerebrosidase unter anwendung der analoga |
| EP02743752A EP1408045B1 (en) | 2001-06-28 | 2002-06-27 | Novel galactosylceramide analogs and beta-glucocerebrosidase activators,external skin preparations and method of activating beta-glucocerebrosidase using the analogs |
| CNB028131487A CN1247605C (zh) | 2001-06-28 | 2002-06-27 | 新型半乳糖苷神经酰胺类似体、使用这些类似体的β－葡糖脑苷酯酶活化剂、皮肤外用药以及β－葡糖脑苷酯酶的活化方法 |
| US11/651,978 US20070111951A1 (en) | 2001-06-28 | 2007-01-11 | Novel galactosylceramide analogues, and beta-glucocerebrosidase activator, external skin preparations and method of activating beta-glucocerebrosidase using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001196016A JP4070966B2 (ja) | 2001-06-28 | 2001-06-28 | 新規ガラクトシルセラミド類縁体及び用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003012684A JP2003012684A (ja) | 2003-01-15 |
| JP4070966B2 true JP4070966B2 (ja) | 2008-04-02 |
Family
ID=19033898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001196016A Expired - Lifetime JP4070966B2 (ja) | 2001-06-28 | 2001-06-28 | 新規ガラクトシルセラミド類縁体及び用途 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7183261B2 (enExample) |
| EP (1) | EP1408045B1 (enExample) |
| JP (1) | JP4070966B2 (enExample) |
| KR (1) | KR100739250B1 (enExample) |
| CN (1) | CN1247605C (enExample) |
| DE (1) | DE60232449D1 (enExample) |
| TW (2) | TWI322151B (enExample) |
| WO (1) | WO2003002584A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101936685B1 (ko) * | 2011-11-16 | 2019-01-11 | (주)아모레퍼시픽 | 글리코실 세라마이드 유사 화합물, 이의 제조방법 및 이를 함유하는 화장료 조성물 |
| JP5918168B2 (ja) * | 2012-04-27 | 2016-05-18 | 富士フイルム株式会社 | β−グルコセレブロシダーゼ活性増強剤 |
| EP2903622A1 (en) | 2012-10-03 | 2015-08-12 | INSERM - Institut National de la Santé et de la Recherche Médicale | Methods and pharmaceutical compositions for the prophylactic treatment of bacterial superinfections post-influenza with invariant nkt cell agonists |
| KR101589633B1 (ko) * | 2014-09-18 | 2016-02-01 | 한국과학기술연구원 | 당세라마이드 유도체 및 이의 제조방법 |
| KR102662215B1 (ko) | 2014-11-06 | 2024-05-02 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 피라졸로(1,5-a)피리미딘 및 의학적 장애의 치료에서의 그의 용도 |
| ES2958391T3 (es) | 2014-11-06 | 2024-02-08 | Bial R&D Invest S A | Imidazo[1,5-a]pirimidinas sustituidas y su uso en el tratamiento de trastornos médicos |
| US20180185368A1 (en) | 2014-11-06 | 2018-07-05 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| WO2017027848A1 (en) * | 2015-08-12 | 2017-02-16 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Glycosylated peptides with pseudoproline residues and having enhanced half-lives and ability to cross the blood brain barrier |
| EP3344276B1 (en) | 2015-09-03 | 2020-04-22 | The Board of Regents of the University of Oklahoma | Peptide inhibitors of clostridium difficile tcdb toxin |
| KR20230104752A9 (ko) | 2016-04-06 | 2024-11-15 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 피라졸로[1,5-a]피리미디닐 카르복스아미드 화합물및 의학적 장애의 치료에서의 그의 용도 |
| CA3020310A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Pyrrolo[1,2-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| US10787454B2 (en) | 2016-04-06 | 2020-09-29 | BIAL—BioTech Investments, Inc. | Imidazo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| JP7164774B2 (ja) | 2016-05-05 | 2022-11-02 | ビアル－アール・アンド・ディ・インベストメンツ・ソシエダーデ・アノニマ | 置換イミダゾ［１，２－ｂ］ピリダジン、置換イミダゾ［１，５－ｂ］ピリダジン、関連化合物、および医学的障害の治療におけるその使用 |
| EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
| WO2017207040A1 (en) | 2016-06-01 | 2017-12-07 | Vib Vzw | ANTI-CANCER THERAPY USING A LEPTIN ANTAGONIST AND AN iNKT-CELL ACTIVATOR |
| US10933126B2 (en) | 2018-05-03 | 2021-03-02 | The Board Of Regents Of The University Of Oklahoma | Clostridium difficile immunogenic compositions and methods of use |
| FR3147951A1 (fr) * | 2023-04-19 | 2024-10-25 | Paris Sciences Et Lettres | Particules de monosaccharides modifies par une chaine hydrophobe et de cyclodextrine. |
Family Cites Families (4)
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| JPH07110872B2 (ja) * | 1990-09-25 | 1995-11-29 | 株式会社ディ・ディ・エス研究所 | 酸性糖脂質及び微粒子キャリヤー |
| JP2774417B2 (ja) | 1991-08-07 | 1998-07-09 | 株式会社ディ・ディ・エス研究所 | ペプチド骨格を有する分枝鎖型糖複合体及び微粒子キャリヤー |
| IT1271624B (it) | 1994-03-21 | 1997-06-04 | Lifegroup Spa | Derivati glucosidici di n-acil alchilamine capaci di esercitare effetto o neuroprotettivo utilizzabili nelle patologie acute e croniche del sistema nervoso centrale correlate ad eccitotossicita' |
| JP2896321B2 (ja) * | 1994-10-27 | 1999-05-31 | 鐘紡株式会社 | β−グルコセレブロシダーゼの活性化方法 |
-
2001
- 2001-06-28 JP JP2001196016A patent/JP4070966B2/ja not_active Expired - Lifetime
-
2002
- 2002-06-27 EP EP02743752A patent/EP1408045B1/en not_active Expired - Lifetime
- 2002-06-27 US US10/482,110 patent/US7183261B2/en not_active Expired - Lifetime
- 2002-06-27 TW TW091114141A patent/TWI322151B/zh not_active IP Right Cessation
- 2002-06-27 CN CNB028131487A patent/CN1247605C/zh not_active Expired - Lifetime
- 2002-06-27 KR KR1020037016943A patent/KR100739250B1/ko not_active Expired - Lifetime
- 2002-06-27 DE DE60232449T patent/DE60232449D1/de not_active Expired - Lifetime
- 2002-06-27 TW TW098132688A patent/TW201002734A/zh unknown
- 2002-06-27 WO PCT/JP2002/006532 patent/WO2003002584A1/ja not_active Ceased
-
2007
- 2007-01-11 US US11/651,978 patent/US20070111951A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040048381A (ko) | 2004-06-09 |
| DE60232449D1 (de) | 2009-07-09 |
| TW201002734A (en) | 2010-01-16 |
| EP1408045B1 (en) | 2009-05-27 |
| WO2003002584A1 (en) | 2003-01-09 |
| EP1408045A4 (en) | 2005-12-28 |
| JP2003012684A (ja) | 2003-01-15 |
| US20070111951A1 (en) | 2007-05-17 |
| EP1408045A1 (en) | 2004-04-14 |
| CN1247605C (zh) | 2006-03-29 |
| CN1522263A (zh) | 2004-08-18 |
| US20040242499A1 (en) | 2004-12-02 |
| TWI322151B (enExample) | 2010-03-21 |
| US7183261B2 (en) | 2007-02-27 |
| KR100739250B1 (ko) | 2007-07-12 |
| HK1067642A1 (en) | 2005-04-15 |
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