JPS60197697A - スフインゴシン誘導体 - Google Patents

スフインゴシン誘導体

Info

Publication number: JPS60197697A
Authority: JP; Japan
Prior art keywords: formula; acid; compound; group; acyl group
Prior art date: 1983-12-05
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.): Pending

Application number

JP59257317A

Other languages

English (en)

Japanese (ja)

Inventor

ロランド　ツチヤネン

ヴオルフガング　フラエフエル

リカルト　ロベルト　シユミツト

ルドルフ　クラガー

ペーター　ジンマーマン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ICN Switzerland AG

Original Assignee

Solco Basel AG

Priority date (The priority date 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 date listed.)

1983-12-05

Filing date

1984-12-05

Publication date

1985-10-07

1984-12-05 Application filed by Solco Basel AG filed Critical Solco Basel AG

1985-10-07 Publication of JPS60197697A publication Critical patent/JPS60197697A/ja

Status Pending legal-status Critical Current

Links

150000003410 sphingosines Chemical class 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 128
239000000203 mixture Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 28
125000002252 acyl group Chemical group 0.000 claims description 27
-1 pentadecanyl Chemical group 0.000 claims description 23
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
235000014113 dietary fatty acids Nutrition 0.000 claims description 16
239000000194 fatty acid Substances 0.000 claims description 16
229930195729 fatty acid Natural products 0.000 claims description 16
238000004587 chromatography analysis Methods 0.000 claims description 15
150000004665 fatty acids Chemical class 0.000 claims description 15
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 10
208000027418 Wounds and injury Diseases 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
206010052428 Wound Diseases 0.000 claims description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 8
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
235000010233 benzoic acid Nutrition 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 4
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 claims description 4
230000001737 promoting effect Effects 0.000 claims description 4
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
230000029663 wound healing Effects 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 claims description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
208000019155 Radiation injury Diseases 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
208000025865 Ulcer Diseases 0.000 claims description 2
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
238000001640 fractional crystallisation Methods 0.000 claims description 2
229960002510 mandelic acid Drugs 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
230000017423 tissue regeneration Effects 0.000 claims description 2
231100000397 ulcer Toxicity 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims 2
KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 claims 1
206010061459 Gastrointestinal ulcer Diseases 0.000 claims 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
239000002841 Lewis acid Substances 0.000 claims 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
235000009827 Prunus armeniaca Nutrition 0.000 claims 1
244000018633 Prunus armeniaca Species 0.000 claims 1
208000007107 Stomach Ulcer Diseases 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000004020 conductor Substances 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 claims 1
HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 claims 1
208000000718 duodenal ulcer Diseases 0.000 claims 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
150000007517 lewis acids Chemical class 0.000 claims 1
210000003141 lower extremity Anatomy 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 174
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
229940093499 ethyl acetate Drugs 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
239000000047 product Substances 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
239000002609 medium Substances 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
150000001720 carbohydrates Chemical group 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
150000002339 glycosphingolipids Chemical class 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
238000000746 purification Methods 0.000 description 8
WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
239000012528 membrane Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
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 6
238000005160 1H NMR spectroscopy Methods 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
230000032050 esterification Effects 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
239000000499 gel Substances 0.000 description 6
239000003456 ion exchange resin Substances 0.000 description 6
229920003303 ion-exchange polymer Polymers 0.000 description 6
150000002632 lipids Chemical class 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000002270 gangliosides Chemical class 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229910015900 BF3 Inorganic materials 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
UFOOFOUFKSIFCD-KTKRTIGZSA-N 2-hydroxynervonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCC(O)C(O)=O UFOOFOUFKSIFCD-KTKRTIGZSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
210000001124 body fluid Anatomy 0.000 description 3
239000010839 body fluid Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
150000002812 neutral glycosphingolipids Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
150000003904 phospholipids Chemical class 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 description 2
VWCUMTCXBIRRSG-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 VWCUMTCXBIRRSG-UHFFFAOYSA-N 0.000 description 2
POQRWMRXUOPCLD-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 3-O-[(3,4,5-trihydroxyphenyl)carbonyl]-beta-D-galactopyranoside Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(C(O)C=CCCCCCCCCCCCCC)COC1OC(CO)C(O)C(O)C1O POQRWMRXUOPCLD-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
102000001554 Hemoglobins Human genes 0.000 description 2
108010054147 Hemoglobins Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
235000021353 Lignoceric acid Nutrition 0.000 description 2
CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
MSUOLNSQHLHDAS-UHFFFAOYSA-N R-2-Hydroxytetracosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O MSUOLNSQHLHDAS-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000700605 Viruses Species 0.000 description 2
150000001559 benzoic acids Chemical class 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
210000003850 cellular structure Anatomy 0.000 description 2
229930183167 cerebroside Natural products 0.000 description 2
RIZIAUKTHDLMQX-UHFFFAOYSA-N cerebroside D Natural products CCCCCCCCCCCCCCCCC(O)C(=O)NC(C(O)C=CCCC=C(C)CCCCCCCCC)COC1OC(CO)C(O)C(O)C1O RIZIAUKTHDLMQX-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
210000004748 cultured cell Anatomy 0.000 description 2
230000006378 damage Effects 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
210000002615 epidermis Anatomy 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
210000003743 erythrocyte Anatomy 0.000 description 2
FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 2
210000002950 fibroblast Anatomy 0.000 description 2
230000006870 function Effects 0.000 description 2
229930182830 galactose Natural products 0.000 description 2
230000012010 growth Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000002772 monosaccharides Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
210000005036 nerve Anatomy 0.000 description 2
229920001542 oligosaccharide Polymers 0.000 description 2
150000002482 oligosaccharides Chemical group 0.000 description 2
210000000496 pancreas Anatomy 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
238000010791 quenching Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
210000000813 small intestine Anatomy 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000003053 toxin Substances 0.000 description 2
231100000765 toxin Toxicity 0.000 description 2
108700012359 toxins Proteins 0.000 description 2
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 1
QFPVVMKZTVQDTL-UHFFFAOYSA-N (Z)-9-hexadecenal Natural products CCCCCCC=CCCCCCCCC=O QFPVVMKZTVQDTL-UHFFFAOYSA-N 0.000 description 1
YZAZXIUFBCPZGB-QZOPMXJLSA-N (z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YZAZXIUFBCPZGB-QZOPMXJLSA-N 0.000 description 1
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 1
OBCUSTCTKLTMBX-UHFFFAOYSA-N 2-acetyloxy-2-phenylacetic acid Chemical compound CC(=O)OC(C(O)=O)C1=CC=CC=C1 OBCUSTCTKLTMBX-UHFFFAOYSA-N 0.000 description 1
IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 1
OOKSMYZBWRKRGU-UHFFFAOYSA-N 2-benzoyl-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)C(=O)C1=CC=CC=C1 OOKSMYZBWRKRGU-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
ZGOZJDITBOCFPV-UHFFFAOYSA-N 5-acetyl-2-hydroxy-4-methylthiophene-3-carbonitrile Chemical compound CC(=O)C=1SC(O)=C(C#N)C=1C ZGOZJDITBOCFPV-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
235000021357 Behenic acid Nutrition 0.000 description 1
YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
102100024479 Cell division cycle-associated protein 3 Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000032544 Cicatrix Diseases 0.000 description 1
UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
101000980907 Homo sapiens Cell division cycle-associated protein 3 Proteins 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
241001122315 Polites Species 0.000 description 1
206010063562 Radiation skin injury Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
NZHXEWZGTQSYJM-UHFFFAOYSA-N [bromo(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 NZHXEWZGTQSYJM-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000004308 accommodation Effects 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
229940116226 behenic acid Drugs 0.000 description 1
125000002351 beta-D-glucopyranosyloxy group Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000008827 biological function Effects 0.000 description 1
230000001851 biosynthetic effect Effects 0.000 description 1
230000036770 blood supply Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000000872 buffer Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000022131 cell cycle Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229940106189 ceramide Drugs 0.000 description 1
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 1
230000008859 change Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000004146 energy storage Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229960001269 glycine hydrochloride Drugs 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 1
LYOAURRGAXEXGO-GWSMSICGSA-N icosanoic acid;(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O LYOAURRGAXEXGO-GWSMSICGSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
244000309715 mini pig Species 0.000 description 1
230000002297 mitogenic effect Effects 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
YSSVMXHKWSNHLH-UHFFFAOYSA-N octadecenal Natural products CCCCCCC=CCCCCCCCCCC=O YSSVMXHKWSNHLH-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
235000020077 pisco Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000037387 scars Effects 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
230000035939 shock Effects 0.000 description 1
230000008054 signal transmission Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
229930193551 sterin Natural products 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
CBYCSRICVDBHMZ-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCCCCCCCC(O)=O CBYCSRICVDBHMZ-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
KLJFYXOVGVXZKT-CCEZHUSRSA-N trans-hexadec-2-enal Chemical compound CCCCCCCCCCCCC\C=C\C=O KLJFYXOVGVXZKT-CCEZHUSRSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YVBMCPFZLGEMJT-UHFFFAOYSA-N trimethylsilyl 2-[bis(trimethylsilyl)amino]acetate Chemical compound C[Si](C)(C)OC(=O)CN([Si](C)(C)C)[Si](C)(C)C YVBMCPFZLGEMJT-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1

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
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Crystallography & Structural Chemistry (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Dermatology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP59257317A 1983-12-05 1984-12-05 スフインゴシン誘導体 Pending JPS60197697A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH6493/83-6		1983-12-05
CH6493/83A CH679209A5 (en)	1983-12-05	1983-12-05	New neutral glyco-sphingolipid derivs.
CH4671/84-1		1984-09-28

Publications (1)

Publication Number	Publication Date
JPS60197697A true JPS60197697A (ja)	1985-10-07

Family

ID=4310488

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59257317A Pending JPS60197697A (ja)	1983-12-05	1984-12-05	スフインゴシン誘導体

Country Status (4)

Country	Link
JP (1)	JPS60197697A (de)
CH (1)	CH679209A5 (de)
DD (1)	DD232052A5 (de)
ZA (1)	ZA849442B (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0193562A (ja) *	1987-10-05	1989-04-12	Shionogi & Co Ltd	スフィンゴシン誘導体
JPH02200691A (ja) *	1988-12-02	1990-08-08	Fidia Spa	リゾスフィンゴ脂質誘導体
WO2000017216A1 (fr) *	1998-09-21	2000-03-30	Otsuka Pharmaceutical Co., Ltd.	Derives de carboxymethylgalactose

1983
- 1983-12-05 CH CH6493/83A patent/CH679209A5/de not_active IP Right Cessation
1984
- 1984-12-03 DD DD84270215A patent/DD232052A5/de unknown
- 1984-12-04 ZA ZA849442A patent/ZA849442B/xx unknown
- 1984-12-05 JP JP59257317A patent/JPS60197697A/ja active Pending

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL&PHARMACEUTICAL BULLETIN=1983 *
JOURNAL OF BIOCHEMISTRY(TOKYO)=1982 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0193562A (ja) *	1987-10-05	1989-04-12	Shionogi & Co Ltd	スフィンゴシン誘導体
JPH02200691A (ja) *	1988-12-02	1990-08-08	Fidia Spa	リゾスフィンゴ脂質誘導体
WO2000017216A1 (fr) *	1998-09-21	2000-03-30	Otsuka Pharmaceutical Co., Ltd.	Derives de carboxymethylgalactose
US6503885B1 (en)	1998-09-21	2003-01-07	Otsuka Pharmaceutical Co., Ltd.	Carboxymethylgalactose derivatives
JP4553488B2 (ja) *	1998-09-21	2010-09-29	大塚製薬株式会社	カルボキシメチルガラクトース誘導体

Also Published As

Publication number	Publication date
ZA849442B (en)	1985-07-31
DD232052A5 (de)	1986-01-15
CH679209A5 (en)	1992-01-15

Publication	Publication Date	Title
US4952683A (en)	1990-08-28	Process for the preparation of sphingosine derivatives
IT8448492A1 (it)	1986-01-03	Derivati di gangliosidi
WO2012025857A1 (en)	2012-03-01	Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors
US4454123A (en)	1984-06-12	O-xylopyranoside series compounds and methods of use
JPH03163091A (ja)	1991-07-15	１，２―Ｏ―イソプロピリデン―α，Ｄ―グルコフラノースの３，５，６―置換誘導体類及びそれらの誘導体を調製するための中間体
Wilson et al.	1995	n-Pentenyl glycoside based methodology for determining the relative reactivities of variously protected pairs of glycosides
US5962660A (en)	1999-10-05	Sialyl Lewis X mimetics incorporating fucopeptides
US4730058A (en)	1988-03-08	Sialosylceramides and production method thereof
DE69523889T2 (de)	2002-07-04	Gangliosid gm3 analog mit einem an der position 9 fluorierten sialinsäurerest und zwischenstufe dafür
HU197916B (en)	1989-06-28	Process for producing sphingosine derivatives
JPS60197697A (ja)	1985-10-07	スフインゴシン誘導体
Hashihayata et al.	2003	Convergent total syntheses of oligosaccharides by one-pot sequential stereoselective glycosylations
JPH0249795A (ja)	1990-02-20	ガングリオシド類の新規な製造法
Berkin et al.	2000	Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose and their effects on glycoconjugate biosynthesis
DK170170B1 (da)	1995-06-06	Alfa-D-Glucopyranosederivater, fremgangsmåde til fremstilling og farmaceutisk komposition med indhold deraf
EP1711508B1 (de)	2009-01-28	6r-(3,6-didesoxy-l-arabinohexopyranosyloxy)heptansäure, verfahren zu deren herstellung und deren dauerwirkung
DE3219209A1 (de)	1982-12-09	N-acetylneuraminsaeure-derivate
Ueda et al.	1999	Syntheses and novel bioactivities of artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty
US5643885A (en)	1997-07-01	Etoposide derivatives, process for preparing them, their use as a medicinal product and their use for the preparation of a medicinal product intended for anti-cancer treatment
US5453500A (en)	1995-09-26	Water-soluble glycosylated derivatives of 1,2-dithiin compounds
DE69614371T2 (de)	2002-05-16	Fluorierte gangliosid-gm3-analoge und ihre zwischenprodukte
US6245902B1 (en)	2001-06-12	C-glycoside analogs and methods for their preparation and use
JPH02292295A (ja)	1990-12-03	エトポシドの製造方法
Mochizuki et al.	2000	Lipid A-type pyrancarboxylic acid derivatives, their synthesis and their biological activities
CA2062369A1 (en)	1992-09-30	Thioglycoside analogs of gangliosides