SK141695A3 - Analogous compound sialyl lex, pharmaceutical agent containing this compound and method of preparation of lactoseammoniacal salt - Google Patents

Info

Publication number

SK141695A3

SK141695A3 SK1416-95A SK141695A SK141695A3 SK 141695 A3 SK141695 A3 SK 141695A3 SK 141695 A SK141695 A SK 141695A SK 141695 A3 SK141695 A3 SK 141695A3

Authority

SK

Slovakia

Prior art keywords

group

compound

alkyl

hydrogen

alkylene

Prior art date

1993-05-14

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 174
• 150000003839 salts Chemical class 0.000 title claims description 21
• 238000000034 method Methods 0.000 title abstract description 43
• 238000002360 preparation method Methods 0.000 title abstract description 10
• 239000008177 pharmaceutical agent Substances 0.000 title 1
• 125000003118 aryl group Chemical group 0.000 claims abstract description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 17
• 125000005630 sialyl group Chemical group 0.000 claims abstract description 12
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
• -1 sialyl Le x Chemical compound 0.000 claims description 122
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 38
• 229960000511 lactulose Drugs 0.000 claims description 37
• PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 claims description 37
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 36
• JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 26
• 239000002904 solvent Substances 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 239000011541 reaction mixture Substances 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 150000002772 monosaccharides Chemical class 0.000 claims description 19
• 150000001720 carbohydrates Chemical class 0.000 claims description 16
• 150000002016 disaccharides Chemical class 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 150000003141 primary amines Chemical class 0.000 claims description 15
• 229930182474 N-glycoside Natural products 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 10
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 230000021164 cell adhesion Effects 0.000 claims description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
• 208000036822 Small cell carcinoma of the ovary Diseases 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 201000005292 ovarian small cell carcinoma Diseases 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 150000003973 alkyl amines Chemical class 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 238000002156 mixing Methods 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 239000000376 reactant Substances 0.000 claims description 5
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 125000004001 thioalkyl group Chemical group 0.000 claims description 4
• 150000001735 carboxylic acids Chemical class 0.000 claims description 2
• 230000002829 reductive effect Effects 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
• 235000004789 Rosa xanthina Nutrition 0.000 claims 1
• 241000109329 Rosa xanthina Species 0.000 claims 1
• SFZBBUSDVJSDGR-XWFYHZIMSA-N beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp 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@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O[C@H]2[C@H]([C@@H](CO)O[C@@H](O)[C@@H]2O)O)[C@@H]1NC(C)=O SFZBBUSDVJSDGR-XWFYHZIMSA-N 0.000 claims 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
• 230000033764 rhythmic process Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 65
• 108090000184 Selectins Proteins 0.000 abstract description 25
• 102000003800 Selectins Human genes 0.000 abstract description 24
• 239000003112 inhibitor Substances 0.000 abstract description 23
• OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 abstract description 7
• 239000000543 intermediate Substances 0.000 abstract description 7
• OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 abstract description 6
• MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 abstract description 6
• 230000001413 cellular effect Effects 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
• 239000000243 solution Substances 0.000 description 78
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
• 210000004027 cell Anatomy 0.000 description 74
• 238000006243 chemical reaction Methods 0.000 description 65
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 52
• 238000005160 1H NMR spectroscopy Methods 0.000 description 46
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
• 239000007787 solid Substances 0.000 description 40
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
• 108010024212 E-Selectin Proteins 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 102100023471 E-selectin Human genes 0.000 description 31
• 230000027455 binding Effects 0.000 description 31
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 238000003786 synthesis reaction Methods 0.000 description 28
• 239000000047 product Substances 0.000 description 26
• 238000003556 assay Methods 0.000 description 25
• 230000015572 biosynthetic process Effects 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 239000002253 acid Substances 0.000 description 24
• 239000000463 material Substances 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• 229940125898 compound 5 Drugs 0.000 description 22
• 239000003446 ligand Substances 0.000 description 21
• 235000002639 sodium chloride Nutrition 0.000 description 21
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
• 108090000623 proteins and genes Proteins 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 16
• SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• 108010035766 P-Selectin Proteins 0.000 description 14
• 102100023472 P-selectin Human genes 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 14
• SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 102000004190 Enzymes Human genes 0.000 description 13
• 108090000790 Enzymes Proteins 0.000 description 13
• PNIWLNAGKUGXDO-UHFFFAOYSA-N Lactosamine Natural products OC1C(N)C(O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 PNIWLNAGKUGXDO-UHFFFAOYSA-N 0.000 description 13
• 238000007792 addition Methods 0.000 description 13
• 229940088598 enzyme Drugs 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 12
• DOVBXGDYENZJBJ-ONMPCKGSSA-N lactosamine Chemical compound O=C[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O DOVBXGDYENZJBJ-ONMPCKGSSA-N 0.000 description 12
• 102000004169 proteins and genes Human genes 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 230000000903 blocking effect Effects 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 210000000265 leukocyte Anatomy 0.000 description 11
• 210000000440 neutrophil Anatomy 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 10
• 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 description 10
• 229910052786 argon Inorganic materials 0.000 description 10
• AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 10
• PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 9
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• 238000001914 filtration Methods 0.000 description 9
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 8
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• 230000004044 response Effects 0.000 description 8
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 7
• 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 7
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• 229940126142 compound 16 Drugs 0.000 description 7
• 229940126214 compound 3 Drugs 0.000 description 7
• 210000002889 endothelial cell Anatomy 0.000 description 7
• 230000002255 enzymatic effect Effects 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 7
• 230000001404 mediated effect Effects 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
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• 239000006188 syrup Substances 0.000 description 7
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• 210000001519 tissue Anatomy 0.000 description 7
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• 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
• 125000006823 (C1-C6) acyl group Chemical group 0.000 description 6
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
• 239000005695 Ammonium acetate Substances 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 6
• 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 6
• SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 229940043376 ammonium acetate Drugs 0.000 description 6
• 235000019257 ammonium acetate Nutrition 0.000 description 6
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 6
• 229940126543 compound 14 Drugs 0.000 description 6
• 229940125782 compound 2 Drugs 0.000 description 6
• 230000008034 disappearance Effects 0.000 description 6
• 238000004090 dissolution Methods 0.000 description 6
• 229930182470 glycoside Natural products 0.000 description 6
• 230000003993 interaction Effects 0.000 description 6
• 239000008101 lactose Substances 0.000 description 6
• 239000002808 molecular sieve Substances 0.000 description 6
• 239000000123 paper Substances 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
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• 230000009467 reduction Effects 0.000 description 6
• 238000006722 reduction reaction Methods 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 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
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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