JP4262480B2 - 結合能を有するシアリル・ルイスｘ類似物 - Google Patents
結合能を有するシアリル・ルイスｘ類似物 Download PDFInfo
- Publication number
- JP4262480B2 JP4262480B2 JP2002563162A JP2002563162A JP4262480B2 JP 4262480 B2 JP4262480 B2 JP 4262480B2 JP 2002563162 A JP2002563162 A JP 2002563162A JP 2002563162 A JP2002563162 A JP 2002563162A JP 4262480 B2 JP4262480 B2 JP 4262480B2
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- JP
- Japan
- Prior art keywords
- compound
- benzyl
- hydrogen
- moiety
- acetyl
- 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
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- NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical class O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O NIGUVXFURDGQKZ-UQTBNESHSA-N 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 108090000184 Selectins Proteins 0.000 claims description 32
- 102000003800 Selectins Human genes 0.000 claims description 31
- 239000003446 ligand Substances 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 125000005630 sialyl group Chemical group 0.000 claims description 21
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 20
- 239000002502 liposome Substances 0.000 claims description 15
- 230000002285 radioactive effect Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229940127089 cytotoxic agent Drugs 0.000 claims description 11
- 150000003904 phospholipids Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 9
- 150000004044 tetrasaccharides Chemical class 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 150000002016 disaccharides Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000005298 paramagnetic effect Effects 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000004043 trisaccharides Chemical class 0.000 claims description 6
- 239000002872 contrast media Substances 0.000 claims description 5
- 239000002254 cytotoxic agent Substances 0.000 claims description 5
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 238000003745 diagnosis Methods 0.000 claims description 3
- 125000002566 glucosaminyl group Chemical group 0.000 claims description 3
- 238000001959 radiotherapy Methods 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000002059 diagnostic imaging Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000600 disaccharide group Chemical group 0.000 claims 1
- 239000002961 echo contrast media Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 239000000203 mixture Substances 0.000 description 50
- 239000000243 solution Substances 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 37
- -1 tetrasaccharide compounds Chemical class 0.000 description 37
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 238000011282 treatment Methods 0.000 description 20
- 230000008685 targeting Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- OMRLTNCLYHKQCK-DHGKCCLASA-N 4-nitrophenyl N-acetyl-beta-D-glucosaminide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C([N+]([O-])=O)C=C1 OMRLTNCLYHKQCK-DHGKCCLASA-N 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- LAQPKDLYOBZWBT-NYLDSJSYSA-N (2s,4s,5r,6r)-5-acetamido-2-{[(2s,3r,4s,5s,6r)-2-{[(2r,3r,4r,5r)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1r,2r)-1,2,3-trihydrox Chemical class O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]([C@@H](NC(C)=O)C=O)[C@@H]([C@H](O)CO)O[C@H]1[C@H](O)[C@@H](O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O1 LAQPKDLYOBZWBT-NYLDSJSYSA-N 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 230000021164 cell adhesion Effects 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 230000006870 function Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- 238000005259 measurement Methods 0.000 description 12
- YRAQXZMHYZXWBZ-OGPNLZSQSA-N (3s,4r,5r,6s)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol Chemical compound O([C@@H]1C(O)O[C@H]([C@H]([C@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)C)CC1=CC=CC=C1 YRAQXZMHYZXWBZ-OGPNLZSQSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 210000000265 leukocyte Anatomy 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- MJZXQAVNDOYDAP-RBGCBHJMSA-N (2s,3s,4r,5r,6s)-2-bromo-6-methyl-3,4,5-tris(phenylmethoxy)oxane Chemical compound O([C@@H]1[C@H](Br)O[C@H]([C@H]([C@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)C)CC1=CC=CC=C1 MJZXQAVNDOYDAP-RBGCBHJMSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 206010061218 Inflammation Diseases 0.000 description 9
- 230000004054 inflammatory process Effects 0.000 description 9
- 125000005647 linker group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000002246 antineoplastic agent Substances 0.000 description 8
- 239000000032 diagnostic agent Substances 0.000 description 8
- 229940039227 diagnostic agent Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 7
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
- 235000014633 carbohydrates Nutrition 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- 150000003254 radicals Chemical class 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 6
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 6
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 6
- 108010024212 E-Selectin Proteins 0.000 description 6
- 102100023471 E-selectin Human genes 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 229940126543 compound 14 Drugs 0.000 description 6
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- 238000001514 detection method Methods 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 6
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 5
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 5
- 0 CC(C(C(C1OCc2ccccc2)OCc2ccccc2)OCc2ccccc2)OC1OC(C(C(Oc(cc1)ccc1[N+]([O-])=O)OC1COCc2ccccc2)NC(C)=O)C1OC(C(C1OC(C2)(C(OC)=O)OC([C@@]([C@@](COC(C)=O)OC(C)=O)OC(C)=O)C(*)C2OC(C)=O)O)OC(COCc2ccccc2)C1O Chemical compound CC(C(C(C1OCc2ccccc2)OCc2ccccc2)OCc2ccccc2)OC1OC(C(C(Oc(cc1)ccc1[N+]([O-])=O)OC1COCc2ccccc2)NC(C)=O)C1OC(C(C1OC(C2)(C(OC)=O)OC([C@@]([C@@](COC(C)=O)OC(C)=O)OC(C)=O)C(*)C2OC(C)=O)O)OC(COCc2ccccc2)C1O 0.000 description 5
- 229940126657 Compound 17 Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 5
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 5
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 5
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- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 5
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 5
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 4
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
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Applications Claiming Priority (2)
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|---|---|---|---|
| US25023800P | 2000-11-29 | 2000-11-29 | |
| PCT/US2001/044590 WO2002062810A2 (en) | 2000-11-29 | 2001-11-29 | Linkable sialyl lewis x analogs |
Publications (3)
| Publication Number | Publication Date |
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| JP2004518704A JP2004518704A (ja) | 2004-06-24 |
| JP2004518704A5 JP2004518704A5 (https=) | 2006-01-12 |
| JP4262480B2 true JP4262480B2 (ja) | 2009-05-13 |
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| Country | Link |
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| US (4) | US7422733B2 (https=) |
| EP (1) | EP1337539A2 (https=) |
| JP (1) | JP4262480B2 (https=) |
| AU (1) | AU2002251678A1 (https=) |
| CA (1) | CA2429781C (https=) |
| WO (1) | WO2002062810A2 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5183010B2 (ja) | 2002-05-16 | 2013-04-17 | グリコミメティクス， インコーポレイテッド | セレクチンによって媒介される機能を阻害するための化合物および方法 |
| WO2005051920A2 (en) | 2003-11-19 | 2005-06-09 | Glycomimetics, Inc. | Specific antagonist for both e- and p-selectins |
| US7205385B2 (en) * | 2004-11-12 | 2007-04-17 | General Electric Company | Polymerization method for the synthesis of polypeptide imaging agents |
| EP1928892B1 (en) | 2005-08-09 | 2011-10-12 | GlycoMimetics, Inc. | Glycomimetic inhibitors of the pa-il lectin, pa-iil lectin or both the lectins from pseudomonas |
| GB0517077D0 (en) * | 2005-08-19 | 2005-09-28 | Isis Innovation | Imaging agent |
| SI2264043T1 (en) | 2005-09-02 | 2018-01-31 | Glycomimetics, Inc. | HETEROBIFUNCTIONAL PAN-SELECTINE INHIBITORS |
| US8986650B2 (en) | 2005-10-07 | 2015-03-24 | Guerbet | Complex folate-NOTA-Ga68 |
| EP1940841B9 (fr) | 2005-10-07 | 2017-04-19 | Guerbet | Composes comprenant une partie de reconnaissance d'une cible biologique, couplee a une partie de signal capable de complexer le gallium |
| WO2009126556A1 (en) | 2008-04-08 | 2009-10-15 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| FR2942227B1 (fr) | 2009-02-13 | 2011-04-15 | Guerbet Sa | Utilisation de tampons pour la complexation de radionucleides |
| WO2010126888A1 (en) * | 2009-05-01 | 2010-11-04 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectins and cxcr4 chemokine receptors |
| US8921328B2 (en) | 2010-09-14 | 2014-12-30 | Glycomimetics, Inc. | E-selectin antagonists |
| WO2012061662A1 (en) * | 2010-11-03 | 2012-05-10 | Glycomimetics, Inc. | Glycomimetic-peptidomimetic inhibitors of e-selectins and cxcr4 chemokine receptors |
| WO2012060718A1 (en) * | 2010-11-05 | 2012-05-10 | Sally Diana Poppitt | Preventing or treating metabolic syndrome by administering a trans fatty acid, or a salt, ester or precursor thereof, or sialic acid in free or bound form |
| FR2968999B1 (fr) | 2010-12-20 | 2013-01-04 | Guerbet Sa | Nanoemulsion de chelate pour irm |
| FR2980364B1 (fr) | 2011-09-26 | 2018-08-31 | Guerbet | Nanoemulsions et leur utilisation comme agents de contraste |
| PT2794626T (pt) | 2011-12-22 | 2018-01-12 | Glycomimetics Inc | Compostos de antagonistas de e-selectina |
| CA2891514C (en) | 2012-12-07 | 2020-08-25 | Glycomimetics, Inc. | Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells |
| FR3001154B1 (fr) | 2013-01-23 | 2015-06-26 | Guerbet Sa | Magneto-emulsion vectorisee |
| ES2904533T3 (es) | 2013-12-06 | 2022-04-05 | Aoa Dx | Compuesto antigangliósido para dirigirlo contra el cáncer y generar anticuerpos |
| ES2754549T3 (es) | 2014-12-03 | 2020-04-20 | Glycomimetics Inc | Inhibidores heterobifuncionales de E-selectinas y receptores de quimioquinas CXCR4 |
| EP3170832A1 (en) | 2015-11-17 | 2017-05-24 | Centre National De La Recherche Scientifique | Method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-d-mannose |
| JP2019502727A (ja) | 2016-01-22 | 2019-01-31 | グリコミメティクス， インコーポレイテッド | Ｐａ−ｉｌおよび／またはｐａ−ｉｉｌレクチンの糖模倣体阻害剤 |
| WO2017151708A1 (en) | 2016-03-02 | 2017-09-08 | Glycomimetics, Inc. | Methods for the treatment and/or prevention of cardiovescular disease by inhibition of e-selectin |
| EP3497131B1 (en) | 2016-08-08 | 2022-03-09 | GlycoMimetics, Inc. | Combination of t-cell checkpoint inhibitors with inhibitors of e-selectin or cxcr4, or with heterobifunctional inhibitors of both e-selectin and cxcr4. |
| US11072625B2 (en) | 2016-10-07 | 2021-07-27 | Glycomimetics, Inc. | Highly potent multimeric e-selectin antagonists |
| WO2018112669A1 (en) | 2016-12-23 | 2018-06-28 | Realist Pharma, Inc. | Ganglioside carbohydrate structures and uses thereof |
| CA3054605A1 (en) | 2017-03-15 | 2018-09-20 | Glycomimetics, Inc. | Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists |
| WO2019108750A1 (en) | 2017-11-30 | 2019-06-06 | Glycomimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| CN111566117A (zh) | 2017-12-29 | 2020-08-21 | 糖模拟物有限公司 | E-选择蛋白和半乳凝素-3的异双功能抑制剂 |
| WO2019173229A1 (en) | 2018-03-05 | 2019-09-12 | Glycomimetics, Inc. | Methods for treating acute myeloid leukemia and related conditions |
| WO2020007822A1 (en) | 2018-07-02 | 2020-01-09 | Conservatoire National Des Arts Et Metiers (Cnam) | Bismuth metallic (0) nanoparticles, process of manufacturing and uses thereof |
| US11845771B2 (en) | 2018-12-27 | 2023-12-19 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CA3223246A1 (fr) * | 2021-06-22 | 2022-12-29 | Pauline Poinot | Sondes a base de composes organiques volatils et leurs utilisations pour le diagnostic et le pronostic de pathologies |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1260393A (en) * | 1984-10-16 | 1989-09-26 | Lajos Tarcsay | Liposomes of synthetic lipids |
| US5776093A (en) * | 1985-07-05 | 1998-07-07 | Immunomedics, Inc. | Method for imaging and treating organs and tissues |
| MX174467B (es) * | 1986-01-23 | 1994-05-17 | Squibb & Sons Inc | 1,4,7-triscarboximetil-1,4,7,10-tetraazaciclodo decano substituido en 1 y compuestos analogos |
| WO1992022563A1 (en) | 1991-06-10 | 1992-12-23 | Alberta Research Council | Modified sialyl lewisa compounds |
| EP0589951A1 (en) | 1991-06-10 | 1994-04-06 | Glycomed Incorporated | Modified sialyl lewis?x compounds |
| GB9309513D0 (en) | 1993-05-08 | 1993-06-23 | Univ Coventry | Electrochemical method of modifying biomolecules in particular proteins |
| RO117533B1 (ro) * | 1993-05-14 | 2002-04-30 | Cytel Corp San Diego | DERIVATI DE ANALOGI SIALIL LeX INHIBITORI AI ADEZIUNII CELULARE SI COMPOZITIE FARMACEUTICA CU ACESTIA |
| US5608110A (en) * | 1993-06-15 | 1997-03-04 | Bracco International B.V. | Heteroatom-bearing ligands and metal complexes thereof |
| US5662885A (en) * | 1994-07-22 | 1997-09-02 | Resolution Pharmaceuticals Inc. | Peptide derived radionuclide chelators |
| US6132764A (en) * | 1994-08-05 | 2000-10-17 | Targesome, Inc. | Targeted polymerized liposome diagnostic and treatment agents |
| US6331289B1 (en) * | 1996-10-28 | 2001-12-18 | Nycomed Imaging As | Targeted diagnostic/therapeutic agents having more than one different vectors |
-
2001
- 2001-11-29 WO PCT/US2001/044590 patent/WO2002062810A2/en not_active Ceased
- 2001-11-29 JP JP2002563162A patent/JP4262480B2/ja not_active Expired - Lifetime
- 2001-11-29 CA CA2429781A patent/CA2429781C/en not_active Expired - Lifetime
- 2001-11-29 AU AU2002251678A patent/AU2002251678A1/en not_active Abandoned
- 2001-11-29 EP EP01999154A patent/EP1337539A2/en not_active Withdrawn
- 2001-11-29 US US10/432,914 patent/US7422733B2/en not_active Expired - Lifetime
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2008
- 2008-08-13 US US12/190,857 patent/US20080300220A1/en not_active Abandoned
-
2011
- 2011-05-26 US US13/116,828 patent/US20110229409A1/en not_active Abandoned
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2012
- 2012-04-26 US US13/456,747 patent/US20120258043A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7422733B2 (en) | 2008-09-09 |
| EP1337539A2 (en) | 2003-08-27 |
| WO2002062810A2 (en) | 2002-08-15 |
| JP2004518704A (ja) | 2004-06-24 |
| WO2002062810A3 (en) | 2003-02-13 |
| US20110229409A1 (en) | 2011-09-22 |
| US20040097403A1 (en) | 2004-05-20 |
| CA2429781A1 (en) | 2002-08-15 |
| AU2002251678A1 (en) | 2002-08-19 |
| CA2429781C (en) | 2011-01-11 |
| US20120258043A1 (en) | 2012-10-11 |
| US20080300220A1 (en) | 2008-12-04 |
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