CN103408606B - N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途 - Google Patents

N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途 Download PDF

Info

Publication number: CN103408606B
Authority: CN; China
Prior art keywords: gal; glcn; ethanoyl; compound; deoxidation
Prior art date: 2013-08-21
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.): Active

Application number

CN201310367839.4A

Other languages

English (en)

Chinese (zh)

Other versions

CN103408606A (zh

Inventor

徐云根

姚硕魏

刘坤

董缙

朱启华

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.)

China Pharmaceutical University

Original Assignee

China Pharmaceutical University

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.)

2013-08-21

Filing date

2013-08-21

Publication date

2016-04-27

2013-08-21 Application filed by China Pharmaceutical University filed Critical China Pharmaceutical University

2013-08-21 Priority to CN201310367839.4A priority Critical patent/CN103408606B/zh

2013-11-27 Publication of CN103408606A publication Critical patent/CN103408606A/zh

2016-04-27 Application granted granted Critical

2016-04-27 Publication of CN103408606B publication Critical patent/CN103408606B/zh

Status Active legal-status Critical Current

2033-08-21 Anticipated expiration legal-status Critical

Links

HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title abstract description 3
238000002360 preparation method Methods 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 36
206010028980 Neoplasm Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
230000002491 angiogenic effect Effects 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
208000037976 chronic inflammation Diseases 0.000 claims description 2
208000037893 chronic inflammatory disorder Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
210000003711 chorioallantoic membrane Anatomy 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 7
230000015572 biosynthetic process Effects 0.000 abstract description 5
230000004663 cell proliferation Effects 0.000 abstract description 5
210000003556 vascular endothelial cell Anatomy 0.000 abstract description 5
230000001629 suppression Effects 0.000 abstract description 2
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 53
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 45
FZHXIRIBWMQPQF-UHFFFAOYSA-N Glc-NH2 Natural products O=CC(N)C(O)C(O)C(O)CO FZHXIRIBWMQPQF-UHFFFAOYSA-N 0.000 description 43
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000243 solution Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
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 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
229920000669 heparin Polymers 0.000 description 6
229960002897 heparin Drugs 0.000 description 6
239000007788 liquid Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
230000006837 decompression Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
210000001161 mammalian embryo Anatomy 0.000 description 4
238000000034 method Methods 0.000 description 4
230000000452 restraining effect Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000287828 Gallus gallus Species 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000002390 adhesive tape Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
210000002889 endothelial cell Anatomy 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 3
210000003606 umbilical vein Anatomy 0.000 description 3
230000004862 vasculogenesis Effects 0.000 description 3
-1 vibration layering Substances 0.000 description 3
VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 description 2
NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 2
108090000379 Fibroblast growth factor 2 Proteins 0.000 description 2
102000003974 Fibroblast growth factor 2 Human genes 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 2
150000003926 acrylamides Chemical class 0.000 description 2
229940121369 angiogenesis inhibitor Drugs 0.000 description 2
239000004037 angiogenesis inhibitor Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
210000001136 chorion Anatomy 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000003113 dilution method Methods 0.000 description 2
150000002016 disaccharides Chemical group 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
229960002442 glucosamine Drugs 0.000 description 2
229940088013 hycamtin Drugs 0.000 description 2
210000000994 inner shell membrane Anatomy 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
230000019491 signal transduction Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
229950004288 tosilate Drugs 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
SCJHPUGWYHCYAZ-UHFFFAOYSA-N 3,5-diethyl-2-propylpyridine Chemical compound CCCC1=NC=C(CC)C=C1CC SCJHPUGWYHCYAZ-UHFFFAOYSA-N 0.000 description 1
MEBWABJHRAYGFW-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Cl)C=C1Cl MEBWABJHRAYGFW-UHFFFAOYSA-N 0.000 description 1
VFQOFJQVKVEXIY-UHFFFAOYSA-N 3-(phenylmethoxycarbonylamino)-3-piperidin-3-ylpropanoic acid Chemical compound C1CCNCC1C(CC(=O)O)NC(=O)OCC1=CC=CC=C1 VFQOFJQVKVEXIY-UHFFFAOYSA-N 0.000 description 1
PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
241000272525 Anas platyrhynchos Species 0.000 description 1
GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
101001051969 Bos taurus Fibroblast growth factor 2 Proteins 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
102000002322 Egg Proteins Human genes 0.000 description 1
108010000912 Egg Proteins Proteins 0.000 description 1
108050007372 Fibroblast Growth Factor Proteins 0.000 description 1
102000018233 Fibroblast Growth Factor Human genes 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
229920002971 Heparan sulfate Polymers 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
108090000190 Thrombin Proteins 0.000 description 1
LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
230000003527 anti-angiogenesis Effects 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
244000309466 calf Species 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
NQBWNECTZUOWID-QSYVVUFSSA-N cinnamyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OC\C=C\C1=CC=CC=C1 NQBWNECTZUOWID-QSYVVUFSSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000009514 concussion Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
210000003278 egg shell Anatomy 0.000 description 1
101150073877 egg-1 gene Proteins 0.000 description 1
229910001651 emery Inorganic materials 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008175 fetal development Effects 0.000 description 1
230000001605 fetal effect Effects 0.000 description 1
229940126864 fibroblast growth factor Drugs 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000002634 heparin fragment Substances 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940059936 lithium bromide Drugs 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
150000002482 oligosaccharides Chemical class 0.000 description 1
238000011275 oncology therapy Methods 0.000 description 1
210000004681 ovum Anatomy 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical class [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000004224 protection Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000012764 semi-quantitative analysis Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
229960004249 sodium acetate Drugs 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960004072 thrombin Drugs 0.000 description 1
230000030968 tissue homeostasis Effects 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000006444 vascular growth Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

CN201310367839.4A 2013-08-21 2013-08-21 N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途 Active CN103408606B (zh)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CN201310367839.4A CN103408606B (zh)	2013-08-21	2013-08-21	N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CN201310367839.4A CN103408606B (zh)	2013-08-21	2013-08-21	N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途

Publications (2)

Publication Number	Publication Date
CN103408606A CN103408606A (zh)	2013-11-27
CN103408606B true CN103408606B (zh)	2016-04-27

Family

ID=49601661

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN201310367839.4A Active CN103408606B (zh)	2013-08-21	2013-08-21	N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途

Country Status (1)

Country	Link
CN (1)	CN103408606B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107973819B (zh) *	2017-11-23	2019-12-17	烟台大学	一种β-磷酰化的硝酸酯化合物及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH09301988A (ja) *	1996-05-17	1997-11-25	Sumitomo Pharmaceut Co Ltd	グルコサミン誘導体
CN1827630A (zh) *	2006-04-04	2006-09-06	天津大学	葡萄糖阿魏酸酰胺及其制备方法
CN101591369A (zh) *	2008-05-30	2009-12-02	徐云根	N-糖基-3-芳基丙烯酰胺衍生物、其制法及其医药用途
CN101591364A (zh) *	2008-05-30	2009-12-02	中国药科大学	氨基糖衍生物、其制法及其医药用途
CN101613380A (zh) *	2009-05-13	2009-12-30	中国药科大学	一种氨基糖衍生物,其制备方法及其医药用途

2013
- 2013-08-21 CN CN201310367839.4A patent/CN103408606B/zh active Active

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH09301988A (ja) *	1996-05-17	1997-11-25	Sumitomo Pharmaceut Co Ltd	グルコサミン誘導体
CN1827630A (zh) *	2006-04-04	2006-09-06	天津大学	葡萄糖阿魏酸酰胺及其制备方法
CN101591369A (zh) *	2008-05-30	2009-12-02	徐云根	N-糖基-3-芳基丙烯酰胺衍生物、其制法及其医药用途
CN101591364A (zh) *	2008-05-30	2009-12-02	中国药科大学	氨基糖衍生物、其制法及其医药用途
CN101613380A (zh) *	2009-05-13	2009-12-30	中国药科大学	一种氨基糖衍生物,其制备方法及其医药用途

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry";Sebastien Fort等;《J. Org. Chem.》;20060819;第71卷;第7146-7154页 *

Also Published As

Publication number	Publication date
CN103408606A (zh)	2013-11-27

Legal Events

Date	Code	Title	Description
2013-11-27	C06	Publication
2013-11-27	PB01	Publication
2013-12-18	C10	Entry into substantive examination
2013-12-18	SE01	Entry into force of request for substantive examination
2016-04-27	C14	Grant of patent or utility model
2016-04-27	GR01	Patent grant
2023-11-17	CP02	Change in the address of a patent holder
2023-11-17	CP02	Change in the address of a patent holder	Address after: Tong Xiang, Gulou District of Nanjing city of Jiangsu Province, No. 24 210009 Patentee after: CHINA PHARMACEUTICAL University Address before: 211200 Kechuang Center, 688 Tianshengqiao Avenue, Yongyang Town, Lishui County, Nanjing City, Jiangsu Province Patentee before: CHINA PHARMACEUTICAL University

Publication	Publication Date	Title
CN103450335B (zh)	2015-09-09	β-咔啉酰色氨酰色氨酰氨基酸苄酯、其合成、抗肿瘤作用及应用
CN103044395B (zh)	2015-03-11	含有地氯雷他定结构的氨基酸类衍生物、其制备方法和用途
Wu et al.	2015	Synthesis and binding affinity analysis of positional thiol analogs of mannopyranose for the elucidation of sulfur in different position
CN106243183B (zh)	2018-11-23	熊果酸-硫化氢供体试剂衍生物及其合成方法
CN103408606B (zh)	2016-04-27	N-(2-脱氧乳糖-2-基)-3-(取代苯基)丙烯酰胺及其医药用途
CN104761572B (zh)	2017-04-12	一叶萩型生物碱二聚体类化合物或其可药用盐及其制法和应用
CN101591364B (zh)	2012-05-23	氨基糖衍生物、其制法及其医药用途
Chervin et al.	2002	Synthesis and biological evaluation of a new sialyl Lewis X mimetic derived from lactose
JPH08183785A (ja)	1996-07-16	エスクレチン誘導体、その製造方法及びマトリックスメタロプロテアーゼ阻害剤
CN109771432A (zh)	2019-05-21	氨基葡萄糖及其衍生物作为抗病毒药物的应用
CN106883277B (zh)	2019-05-03	一类具有抗肿瘤活性的呋咱类no供体型灯盏乙素衍生物及其制备方法和用途
CN108530508A (zh)	2018-09-14	齐墩果烷型氮糖苷化合物及其在制备治疗抗糖尿病药物中的应用
CN103340881B (zh)	2016-06-08	一种寡糖类化合物在神经保护方面的应用
CN110028477A (zh)	2019-07-19	一类布雷菲德菌素a的4-位拼合氮芥衍生物的制备方法和用途
CN104292211A (zh)	2015-01-21	地氯雷他定类一氧化氮供体及其制备方法和用途
CN105017231B (zh)	2018-01-26	多取代吲哚类他汀含氟修饰物及其用途
EP2098238B1 (en)	2012-10-17	Helicobacter pylori growth inhibitor containing a monosaccharide derivative having an n-acetylglucosaminyl-group linked at the alpha position
CN104817519A (zh)	2015-08-05	一类ca-4的衍生物、其制法及其医药用途
CN101613380A (zh)	2009-12-30	一种氨基糖衍生物,其制备方法及其医药用途
WO2020038279A1 (zh)	2020-02-27	取代吡唑类化合物、其制备方法、药物组合物及用途
CN106928292B (zh)	2019-08-30	一类硝酸酯no供体型灯盏乙素衍生物及其制备方法和用途
CN105017230B (zh)	2018-05-22	多取代喹啉类他汀含氟衍生物及其用途
CN109400595A (zh)	2019-03-01	一类含噻吩环的抗癌化合物
CA3064774A1 (en)	2018-11-29	Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase
CN105294458A (zh)	2016-02-03	一种抗肿瘤小分子化合物及其制备方法和应用