CA2224346A1 - Diglycosylated 1,2-diols as mimetics of sialyl-lewis x and sialyl-lewis a - Google Patents
Diglycosylated 1,2-diols as mimetics of sialyl-lewis x and sialyl-lewis a Download PDFInfo
- Publication number
- CA2224346A1 CA2224346A1 CA002224346A CA2224346A CA2224346A1 CA 2224346 A1 CA2224346 A1 CA 2224346A1 CA 002224346 A CA002224346 A CA 002224346A CA 2224346 A CA2224346 A CA 2224346A CA 2224346 A1 CA2224346 A1 CA 2224346A1
- Authority
- CA
- Canada
- Prior art keywords
- c10aryl
- c12alkyl
- substituted
- group
- unsubstituted
- 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.)
- Abandoned
Links
- 150000000180 1,2-diols Chemical class 0.000 title claims description 4
- NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical compound 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 abstract description 5
- XBSNXOHQOTUENA-KRAHZTDDSA-N alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->3)-[alpha-L-Fuc-(1->4)]-D-GlcNAc Chemical compound 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](NC(C)=O)C(O)O[C@@H]1CO XBSNXOHQOTUENA-KRAHZTDDSA-N 0.000 title abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 241
- 239000001257 hydrogen Substances 0.000 claims abstract description 231
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 125000001424 substituent group Chemical group 0.000 claims abstract description 159
- -1 aliphatic 1,2-diol Chemical class 0.000 claims abstract description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 87
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 118
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 102
- 229910052751 metal Inorganic materials 0.000 claims description 88
- 239000002184 metal Substances 0.000 claims description 88
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 81
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
- 229910052799 carbon Inorganic materials 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 69
- 238000002360 preparation method Methods 0.000 claims description 68
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 57
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 43
- 229940124530 sulfonamide Drugs 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 37
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 37
- 150000003456 sulfonamides Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 239000004202 carbamide Substances 0.000 claims description 35
- 235000013877 carbamide Nutrition 0.000 claims description 35
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 32
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 26
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 150000001408 amides Chemical class 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 229910006069 SO3H Inorganic materials 0.000 claims description 14
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 4
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 4
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 2
- 101100240522 Caenorhabditis elegans nhr-18 gene Proteins 0.000 claims description 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000008267 fucoses Chemical class 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 249
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 169
- 229910001868 water Inorganic materials 0.000 description 168
- 239000000243 solution Substances 0.000 description 165
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 123
- 239000011734 sodium Substances 0.000 description 118
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 150000002431 hydrogen Chemical group 0.000 description 96
- 239000000203 mixture Substances 0.000 description 90
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 81
- 239000000741 silica gel Substances 0.000 description 81
- 229910002027 silica gel Inorganic materials 0.000 description 81
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 61
- 239000000706 filtrate Substances 0.000 description 53
- 239000003480 eluent Substances 0.000 description 51
- 229960000583 acetic acid Drugs 0.000 description 50
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 238000010828 elution Methods 0.000 description 47
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 46
- 229940035024 thioglycerol Drugs 0.000 description 43
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 38
- 239000000499 gel Substances 0.000 description 37
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 37
- 239000002245 particle Substances 0.000 description 35
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 34
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 34
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- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 34
- 238000001514 detection method Methods 0.000 description 34
- XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 34
- 238000002523 gelfiltration Methods 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
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- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000012043 crude product Substances 0.000 description 32
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 31
- 235000017557 sodium bicarbonate Nutrition 0.000 description 31
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 30
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- 239000011148 porous material Substances 0.000 description 30
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- 239000000725 suspension Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229910052786 argon Inorganic materials 0.000 description 24
- 239000012300 argon atmosphere Substances 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 238000005406 washing Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
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- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 14
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 14
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 14
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- 150000002500 ions Chemical class 0.000 description 12
- 239000002808 molecular sieve Substances 0.000 description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
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- 150000003053 piperidines Chemical class 0.000 description 11
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 238000005342 ion exchange Methods 0.000 description 10
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 9
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- 101100172504 Caenorhabditis elegans epg-6 gene Proteins 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
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- 238000004809 thin layer chromatography Methods 0.000 description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
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- 150000003951 lactams Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 238000000670 ligand binding assay Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 102220254284 rs755928199 Human genes 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 125000005630 sialyl group Chemical group 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 101150008563 spir gene Proteins 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000005710 tetrahydropyranylene group Chemical group 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07H15/20—Carbocyclic rings
- C07H15/207—Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191495 | 1995-06-29 | ||
| CH1914/95 | 1995-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2224346A1 true CA2224346A1 (en) | 1997-01-16 |
Family
ID=4221546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002224346A Abandoned CA2224346A1 (en) | 1995-06-29 | 1996-06-26 | Diglycosylated 1,2-diols as mimetics of sialyl-lewis x and sialyl-lewis a |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0836610A1 (cs) |
| JP (1) | JPH11508548A (cs) |
| KR (1) | KR19990028543A (cs) |
| CN (1) | CN1196731A (cs) |
| AU (1) | AU707474B2 (cs) |
| BR (1) | BR9609285A (cs) |
| CA (1) | CA2224346A1 (cs) |
| CZ (1) | CZ419797A3 (cs) |
| EA (1) | EA001356B1 (cs) |
| HU (1) | HUP9801805A3 (cs) |
| IL (1) | IL118740A0 (cs) |
| MX (1) | MX9800218A (cs) |
| NO (1) | NO976065L (cs) |
| NZ (1) | NZ311686A (cs) |
| PL (1) | PL324258A1 (cs) |
| SI (1) | SI9620099A (cs) |
| SK (1) | SK177897A3 (cs) |
| TR (1) | TR199701728T1 (cs) |
| WO (1) | WO1997001569A1 (cs) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4564713B2 (ja) | 2000-11-01 | 2010-10-20 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 窒素性複素環式化合物、ならびに窒素性複素環式化合物およびその中間体を作製するための方法 |
| CA2486106C (en) | 2002-05-16 | 2013-07-16 | Glycomimetics, Inc. | Compounds and methods for inhibiting selectin-mediated function |
| DE602004011272T2 (de) | 2003-11-19 | 2008-12-24 | Glycomimetics, Inc. | Spezifischer antagonist sowohl für e- als auch p-selektine |
| EP1577289A1 (en) * | 2004-03-18 | 2005-09-21 | Revotar Biopharmaceuticals AG | Non-glycosylated/-glycosidic/-peptidic small molecule selectin inhibitors for the treament of inflammatory disorders |
| ES2375979T3 (es) | 2005-08-09 | 2012-03-07 | Glycomimetics, Inc. | Inhibidores glicomiméticos de la lectina pa-il, lectina pa-iil o ambas lectinas de pseudomonas. |
| DK1934236T3 (da) * | 2005-09-02 | 2013-02-25 | Glycomimetics Inc | Heterobifunktionelle pan-selektininhibitorer |
| EP1764095A1 (en) | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel nitrocatechol derivatives having selectin ligand activity |
| EP1764093A1 (en) | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel aromatic compounds and their use in medical applications |
| EP1764096A1 (en) | 2005-09-20 | 2007-03-21 | Revotar Biopharmaceuticals AG | Novel phloroglucinol derivatives having selectin ligand activity |
| EP2074132B1 (en) * | 2006-10-12 | 2013-05-15 | GlycoMimetics, Inc. | Glycomimetic replacements for hexoses and n-acetyl hexosamines |
| JP5511390B2 (ja) * | 2007-02-09 | 2014-06-04 | グリコミメティクス， インコーポレイテッド | ヘキソースおよびｎ−アセチルヘキソサミンの置換体を有する糖模倣体の使用方法 |
| WO2009126556A1 (en) | 2008-04-08 | 2009-10-15 | Glycomimetics, Inc. | Pan-selectin inhibitor with enhanced pharmacokinetic activity |
| WO2012037034A1 (en) | 2010-09-14 | 2012-03-22 | Glycomimetics, Inc. | E-selectin antagonists |
| BR112014014547B1 (pt) | 2011-12-22 | 2022-09-27 | Glycomimetics, Inc | Composto, composição e métodos de uso |
| WO2014089269A1 (en) | 2012-12-07 | 2014-06-12 | Glycomimetics, Inc. | Compounds, compositions and methods using e-selectin antagonists for mobilization of hematopoietic cells |
| PL3227310T3 (pl) | 2014-12-03 | 2020-02-28 | Glycomimetics, Inc. | Heterodwufunkcyjne inhibitory selektyn E i receptorów chemokinowych CXCR4” |
| WO2017127422A1 (en) | 2016-01-22 | 2017-07-27 | Glycomimetics, Inc. | Glycomimetic inhibitors of pa-il and pa-iil lectins |
| US11291678B2 (en) | 2016-03-02 | 2022-04-05 | Glycomimetics, Inc | Methods for the treatment and/or prevention of cardiovascular 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. |
| KR20240046288A (ko) | 2016-10-07 | 2024-04-08 | 글리코미메틱스, 인크. | 매우 강력한 다량체성 e-셀렉틴 길항물질 |
| CA3054605A1 (en) | 2017-03-15 | 2018-09-20 | Glycomimetics, Inc. | Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists |
| EP3717013A1 (en) | 2017-11-30 | 2020-10-07 | GlycoMimetics, Inc. | Methods of mobilizing marrow infiltrating lymphocytes and uses thereof |
| US11548908B2 (en) | 2017-12-29 | 2023-01-10 | Glycomimetics, Inc. | Heterobifunctional inhibitors of E-selectin and galectin-3 |
| CA3091454A1 (en) | 2018-03-05 | 2019-09-12 | Glycomimetics, Inc. | Methods for treating acute myeloid leukemia and related conditions |
| WO2020139962A1 (en) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc. | Heterobifunctional inhibitors of e-selectin and galectin-3 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326752A (en) * | 1991-11-27 | 1994-07-05 | Glycomed Incorporated | Substituted lactose and lactosamine derivatives as cell adhesion inhibitors |
| WO1993023031A1 (en) * | 1992-05-08 | 1993-11-25 | The Biomembrane Institute | Multivalent mimetics and peptide mimetics for blocking carbohydrate-dependent cellular interaction and for eliciting anticarbohydrate t-cell response |
| CA2100412A1 (en) * | 1992-07-15 | 1994-01-16 | Yutaka Yamada | Glycolipid derivatives |
-
1996
- 1996-06-26 JP JP9504171A patent/JPH11508548A/ja active Pending
- 1996-06-26 CN CN96196452A patent/CN1196731A/zh active Pending
- 1996-06-26 NZ NZ311686A patent/NZ311686A/xx unknown
- 1996-06-26 TR TR97/01728T patent/TR199701728T1/xx unknown
- 1996-06-26 BR BR9609285A patent/BR9609285A/pt not_active Application Discontinuation
- 1996-06-26 AU AU63053/96A patent/AU707474B2/en not_active Ceased
- 1996-06-26 IL IL11874096A patent/IL118740A0/xx unknown
- 1996-06-26 WO PCT/EP1996/002785 patent/WO1997001569A1/en not_active Application Discontinuation
- 1996-06-26 EP EP96922034A patent/EP0836610A1/en not_active Ceased
- 1996-06-26 HU HU9801805A patent/HUP9801805A3/hu unknown
- 1996-06-26 CZ CZ974197A patent/CZ419797A3/cs unknown
- 1996-06-26 KR KR1019970709861A patent/KR19990028543A/ko not_active Withdrawn
- 1996-06-26 EA EA199800103A patent/EA001356B1/ru not_active IP Right Cessation
- 1996-06-26 PL PL96324258A patent/PL324258A1/xx unknown
- 1996-06-26 CA CA002224346A patent/CA2224346A1/en not_active Abandoned
- 1996-06-26 SI SI9620099A patent/SI9620099A/sl unknown
- 1996-06-26 SK SK1778-97A patent/SK177897A3/sk unknown
-
1997
- 1997-12-23 NO NO976065A patent/NO976065L/no not_active Application Discontinuation
-
1998
- 1998-01-07 MX MX9800218A patent/MX9800218A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11508548A (ja) | 1999-07-27 |
| WO1997001569A1 (en) | 1997-01-16 |
| NO976065D0 (no) | 1997-12-23 |
| MX9800218A (es) | 1998-07-31 |
| NO976065L (no) | 1998-02-17 |
| EP0836610A1 (en) | 1998-04-22 |
| IL118740A0 (en) | 1996-10-16 |
| CN1196731A (zh) | 1998-10-21 |
| AU6305396A (en) | 1997-01-30 |
| TR199701728T1 (xx) | 1998-03-21 |
| AU707474B2 (en) | 1999-07-08 |
| EA001356B1 (ru) | 2001-02-26 |
| SK177897A3 (en) | 1998-08-05 |
| NZ311686A (en) | 2000-01-28 |
| KR19990028543A (ko) | 1999-04-15 |
| SI9620099A (sl) | 1998-08-31 |
| BR9609285A (pt) | 1999-05-11 |
| CZ419797A3 (cs) | 1998-06-17 |
| HUP9801805A3 (en) | 2002-01-28 |
| EA199800103A1 (ru) | 1998-08-27 |
| PL324258A1 (en) | 1998-05-11 |
| HUP9801805A2 (hu) | 1998-12-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
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