JPS63179885A - 新規なグリコピラノース誘導体 - Google Patents
新規なグリコピラノース誘導体Info
- Publication number
- JPS63179885A JPS63179885A JP61287704A JP28770486A JPS63179885A JP S63179885 A JPS63179885 A JP S63179885A JP 61287704 A JP61287704 A JP 61287704A JP 28770486 A JP28770486 A JP 28770486A JP S63179885 A JPS63179885 A JP S63179885A
- Authority
- JP
- Japan
- Prior art keywords
- sulfo
- amino
- deoxy
- formula
- tetradecanoyl
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical class OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims description 7
- 239000004480 active ingredient Substances 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000001419 myristoyl 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])[H] 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 35
- -1 2-deoxy-2-[3R-(9-phenylnonyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-D-glucopyranose Chemical compound 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001402 nonanoyl 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])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000002434 immunopotentiative effect Effects 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 1
- AWJKHXFUZFLRHQ-BFPXFXJNSA-N [(2R,3S,4R,5S)-2-(hydroxymethyl)-5-[[(3R)-3-(8-phenoxyoctanoyloxy)tetradecanoyl]amino]-3-sulfooxyoxan-4-yl] 8-phenoxyoctanoate Chemical compound O(C1=CC=CC=C1)CCCCCCCC(=O)O[C@@H](CC(=O)N[C@H]1CO[C@@H]([C@H]([C@@H]1OC(CCCCCCCOC1=CC=CC=C1)=O)OS(=O)(=O)O)CO)CCCCCCCCCCC AWJKHXFUZFLRHQ-BFPXFXJNSA-N 0.000 claims 1
- RPJNTRIBJCJFFN-NWNGFIJASA-N [(2R,3S,4R,5S)-2-(hydroxymethyl)-5-[[(3R)-3-(9-phenylnonanoyloxy)tetradecanoyl]amino]-3-sulfooxyoxan-4-yl] 9-phenylnonanoate Chemical compound C1(=CC=CC=C1)CCCCCCCCC(=O)O[C@@H](CC(=O)N[C@H]1CO[C@@H]([C@H]([C@@H]1OC(CCCCCCCCC1=CC=CC=C1)=O)OS(=O)(=O)O)CO)CCCCCCCCCCC RPJNTRIBJCJFFN-NWNGFIJASA-N 0.000 claims 1
- NBLSMQARKOUUHU-BFPXFXJNSA-N [(2R,3S,4R,5S)-5-[[(3R)-3-[8-(4-chlorophenoxy)octanoyloxy]tetradecanoyl]amino]-2-(hydroxymethyl)-3-sulfooxyoxan-4-yl] 8-(4-chlorophenoxy)octanoate Chemical compound ClC1=CC=C(OCCCCCCCC(=O)O[C@@H](CC(=O)N[C@H]2CO[C@@H]([C@H]([C@@H]2OC(CCCCCCCOC2=CC=C(C=C2)Cl)=O)OS(=O)(=O)O)CO)CCCCCCCCCCC)C=C1 NBLSMQARKOUUHU-BFPXFXJNSA-N 0.000 claims 1
- HBMULDWCRWFKOK-ZUITZVHVSA-N [(2r,3s,4r,5r,6r)-2-(hydroxymethyl)-6-methoxy-5-[[(3r)-3-(9-phenylnonanoyloxy)tetradecanoyl]amino]-3-sulfooxyoxan-4-yl] 9-phenylnonanoate Chemical compound O([C@H]1[C@H](OS(O)(=O)=O)[C@@H](CO)O[C@@H](OC)[C@@H]1NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCC=1C=CC=CC=1)C(=O)CCCCCCCCC1=CC=CC=C1 HBMULDWCRWFKOK-ZUITZVHVSA-N 0.000 claims 1
- YOQHKHQKPXYKQE-FIBJEGPVSA-N [(3R,4R,5R,6R)-2-amino-2,3-dihydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl] 8-(3,5-dichlorophenoxy)octanoate Chemical compound NC1(O)[C@H](O)[C@@H](OC(CCCCCCCOC2=CC(=CC(=C2)Cl)Cl)=O)[C@H](OS(=O)(=O)O)[C@H](O1)CO YOQHKHQKPXYKQE-FIBJEGPVSA-N 0.000 claims 1
- UWGLPQHVDTYPGS-ZNDAAQBBSA-N [(3r,4r,5s,6r)-2-hydroxy-6-(hydroxymethyl)-3-(9-naphthalen-1-ylnonanoylamino)-5-sulfooxyoxan-4-yl] 9-naphthalen-1-ylnonanoate Chemical compound C1=CC=C2C(CCCCCCCCC(=O)O[C@@H]3[C@@H](NC(=O)CCCCCCCCC=4C5=CC=CC=C5C=CC=4)C(O)O[C@@H]([C@H]3OS(O)(=O)=O)CO)=CC=CC2=C1 UWGLPQHVDTYPGS-ZNDAAQBBSA-N 0.000 claims 1
- SMCBOLXKRXMSMJ-PFIHCWGLSA-N [(3r,4r,5s,6r)-2-hydroxy-6-(hydroxymethyl)-3-[[(3r)-3-(4-phenylbutanoyloxy)tetradecanoyl]amino]-5-sulfooxyoxan-4-yl] 4-phenylbutanoate Chemical compound O([C@H]1[C@H](OS(O)(=O)=O)[C@@H](CO)OC(O)[C@@H]1NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCC=1C=CC=CC=1)C(=O)CCCC1=CC=CC=C1 SMCBOLXKRXMSMJ-PFIHCWGLSA-N 0.000 claims 1
- ZLYPARUUTVMXOG-CSWGJSPASA-N [(3r,4r,5s,6r)-2-hydroxy-6-(hydroxymethyl)-3-[[(3r)-9-phenyl-3-(9-phenylnonanoyloxy)nonanoyl]amino]-5-sulfooxyoxan-4-yl] 9-phenylnonanoate Chemical compound C([C@H](CC(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1OC(=O)CCCCCCCCC=1C=CC=CC=1)OS(O)(=O)=O)CO)OC(=O)CCCCCCCCC=1C=CC=CC=1)CCCCCC1=CC=CC=C1 ZLYPARUUTVMXOG-CSWGJSPASA-N 0.000 claims 1
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001900 immune effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000000694 effects Effects 0.000 description 23
- 230000000704 physical effect Effects 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- 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 9
- 239000002904 solvent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000003308 immunostimulating effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229940104230 thymidine Drugs 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 239000002158 endotoxin Substances 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 description 4
- 229920006008 lipopolysaccharide Polymers 0.000 description 4
- 230000002297 mitogenic effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KWXHHANUUIBIDD-UHFFFAOYSA-N 9-naphthalen-1-ylnonanoic acid Chemical compound C1=CC=C2C(CCCCCCCCC(=O)O)=CC=CC2=C1 KWXHHANUUIBIDD-UHFFFAOYSA-N 0.000 description 2
- 210000002925 A-like Anatomy 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N Tetrahydropalmatine Natural products C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000016396 cytokine production Effects 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000002008 hemorrhagic effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 230000016784 immunoglobulin production Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- HEHQDWUWJVPREQ-XQJZMFRCSA-N lipid X Chemical compound CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC HEHQDWUWJVPREQ-XQJZMFRCSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000012457 nonaqueous media Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000003716 rejuvenation Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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Landscapes
- Pyrane Compounds (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27344085 | 1985-12-06 | ||
| JP60-273440 | 1985-12-06 | ||
| JP61-210379 | 1986-09-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63179885A true JPS63179885A (ja) | 1988-07-23 |
| JPH0474359B2 JPH0474359B2 (enrdf_load_stackoverflow) | 1992-11-26 |
Family
ID=17527940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61287704A Granted JPS63179885A (ja) | 1985-12-06 | 1986-12-04 | 新規なグリコピラノース誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63179885A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191072A (en) * | 1989-09-20 | 1993-03-02 | Japan Tobacco Inc. | Lipid a monosaccharide analogues |
| US5278300A (en) * | 1990-04-12 | 1994-01-11 | Japan Tobacco, Inc. | 4,6-o-hydroxyphosphoryl-glucosamine derivatives |
| JPH0641175A (ja) * | 1992-01-31 | 1994-02-15 | Ono Pharmaceut Co Ltd | グルコピラノース誘導体の塩およびその中間体 |
| WO1999056744A1 (fr) * | 1998-05-06 | 1999-11-11 | Ono Pharmaceutical Co., Ltd. | Immunosuppresseur contenant un derive de glucopyranose comme principe actif |
| JP2009508896A (ja) * | 2005-09-20 | 2009-03-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | 新規カルボン酸誘導体 |
| JP2021512963A (ja) * | 2018-02-12 | 2021-05-20 | イニミューン・コーポレーション | Ｔｏｌｌ様受容体リガンド |
-
1986
- 1986-12-04 JP JP61287704A patent/JPS63179885A/ja active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191072A (en) * | 1989-09-20 | 1993-03-02 | Japan Tobacco Inc. | Lipid a monosaccharide analogues |
| US5278300A (en) * | 1990-04-12 | 1994-01-11 | Japan Tobacco, Inc. | 4,6-o-hydroxyphosphoryl-glucosamine derivatives |
| JPH0641175A (ja) * | 1992-01-31 | 1994-02-15 | Ono Pharmaceut Co Ltd | グルコピラノース誘導体の塩およびその中間体 |
| WO1999056744A1 (fr) * | 1998-05-06 | 1999-11-11 | Ono Pharmaceutical Co., Ltd. | Immunosuppresseur contenant un derive de glucopyranose comme principe actif |
| US6495678B1 (en) | 1998-05-06 | 2002-12-17 | Ono Pharmaceutical Co., Ltd. | Immunosuppressant containing glucopyranose derivative as active ingredient |
| JP2009508896A (ja) * | 2005-09-20 | 2009-03-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | 新規カルボン酸誘導体 |
| JP2021512963A (ja) * | 2018-02-12 | 2021-05-20 | イニミューン・コーポレーション | Ｔｏｌｌ様受容体リガンド |
| JP2024001142A (ja) * | 2018-02-12 | 2024-01-09 | イニミューン・コーポレーション | Ｔｏｌｌ様受容体リガンド |
| US12150948B2 (en) | 2018-02-12 | 2024-11-26 | National Institutes Of Health (Nih), U.S. Dept. Of Health And Human Services (Dhhs), U.S. Government | Toll-like receptor ligands |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0474359B2 (enrdf_load_stackoverflow) | 1992-11-26 |
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