JPS635012B2 - - Google Patents

Info

Publication number

JPS635012B2

JPS635012B2 JP57180053A JP18005382A JPS635012B2 JP S635012 B2 JPS635012 B2 JP S635012B2 JP 57180053 A JP57180053 A JP 57180053A JP 18005382 A JP18005382 A JP 18005382A JP S635012 B2 JPS635012 B2 JP S635012B2

Authority

JP

Japan

Prior art keywords

formula

compound

glcp

group

glucopyranoside

Prior art date

1976-12-23

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

Links

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• Global Dossier
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• 239000000203 mixture Substances 0.000 claims description 58
• -1 glucopyranyl Chemical group 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 239000003085 diluting agent Substances 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 239000002904 solvent Substances 0.000 claims description 16
• 150000002336 glycosamine derivatives Chemical class 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 239000007788 liquid Substances 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 239000007864 aqueous solution Substances 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 239000002775 capsule Substances 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• 239000003826 tablet Substances 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 239000006187 pill Substances 0.000 claims description 5
• 239000004094 surface-active agent Substances 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 4
• 230000007863 steatosis Effects 0.000 claims description 4
• 231100000240 steatosis hepatitis Toxicity 0.000 claims description 4
• 239000000829 suppository Substances 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 3
• 239000007787 solid Substances 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims 2
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
• 239000003708 ampul Substances 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 160
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 238000006243 chemical reaction Methods 0.000 description 49
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
• 239000000243 solution Substances 0.000 description 40
• 238000004949 mass spectrometry Methods 0.000 description 33
• 238000000034 method Methods 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• 239000003112 inhibitor Substances 0.000 description 29
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• 241001465754 Metazoa Species 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 230000000694 effects Effects 0.000 description 23
• 102000004190 Enzymes Human genes 0.000 description 20
• 108090000790 Enzymes Proteins 0.000 description 20
• 229930006000 Sucrose Natural products 0.000 description 20
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 20
• 229940088598 enzyme Drugs 0.000 description 20
• 239000005720 sucrose Substances 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
• 230000002401 inhibitory effect Effects 0.000 description 18
• 239000008194 pharmaceutical composition Substances 0.000 description 17
• 235000019441 ethanol Nutrition 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000007858 starting material Substances 0.000 description 15
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 229920002472 Starch Polymers 0.000 description 12
• 235000019698 starch Nutrition 0.000 description 12
• 235000000346 sugar Nutrition 0.000 description 11
• 150000001720 carbohydrates Chemical class 0.000 description 10
• 235000014633 carbohydrates Nutrition 0.000 description 10
• 150000002500 ions Chemical class 0.000 description 10
• 239000008107 starch Substances 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• 238000004809 thin layer chromatography Methods 0.000 description 10
• 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 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 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 9
• 239000001913 cellulose Substances 0.000 description 9
• 229920002678 cellulose Polymers 0.000 description 9
• 229960001031 glucose Drugs 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 239000008103 glucose Substances 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 235000002639 sodium chloride Nutrition 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
• 239000011230 binding agent Substances 0.000 description 7
• 239000008280 blood Substances 0.000 description 7
• 210000004369 blood Anatomy 0.000 description 7
• 239000003651 drinking water Substances 0.000 description 7
• 235000020188 drinking water Nutrition 0.000 description 7
• 239000003925 fat Substances 0.000 description 7
• 235000019197 fats Nutrition 0.000 description 7
• 238000000338 in vitro Methods 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 229940088594 vitamin Drugs 0.000 description 7
• 239000011782 vitamin Substances 0.000 description 7
• 235000013343 vitamin Nutrition 0.000 description 7
• 229930003231 vitamin Natural products 0.000 description 7
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 6
• 102000013142 Amylases Human genes 0.000 description 6
• 108010065511 Amylases Proteins 0.000 description 6
• 102000004366 Glucosidases Human genes 0.000 description 6
• 108010056771 Glucosidases Proteins 0.000 description 6
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• 238000010521 absorption reaction Methods 0.000 description 6
• 239000013543 active substance Substances 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
• 229930182478 glucoside Natural products 0.000 description 6
• 229910052739 hydrogen Inorganic materials 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 239000011707 mineral Substances 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• 235000018102 proteins Nutrition 0.000 description 6
• 102000004169 proteins and genes Human genes 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000004382 Amylase Substances 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
• 241000287828 Gallus gallus Species 0.000 description 5
• 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 5
• 241000700159 Rattus Species 0.000 description 5
• 241000282887 Suidae Species 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
• 102000004139 alpha-Amylases Human genes 0.000 description 5
• 108090000637 alpha-Amylases Proteins 0.000 description 5
• 229940024171 alpha-amylase Drugs 0.000 description 5
• 235000019418 amylase Nutrition 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000007795 chemical reaction product Substances 0.000 description 5
• 235000013330 chicken meat Nutrition 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 5
• 230000007717 exclusion Effects 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 201000001421 hyperglycemia Diseases 0.000 description 5
• 238000001819 mass spectrum Methods 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 125000003396 thiol group Chemical class [H]S* 0.000 description 5
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• 102000004157 Hydrolases Human genes 0.000 description 4
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• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 238000002835 absorbance Methods 0.000 description 4
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
• 238000009395 breeding Methods 0.000 description 4
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• 239000008298 dragée Substances 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 235000013312 flour Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens Chemical class 0.000 description 4
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 230000000968 intestinal effect Effects 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
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• 229920006395 saturated elastomer Polymers 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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• 208000013016 Hypoglycemia Diseases 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
• 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 240000008042 Zea mays Species 0.000 description 3
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
• 238000006640 acetylation reaction Methods 0.000 description 3
• OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 3
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• XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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• 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 230000002218 hypoglycaemic effect Effects 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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• REULQIKBNNDNDX-UHFFFAOYSA-M sodium;2,3-dihydroxypropyl hydrogen phosphate Chemical compound [Na+].OCC(O)COP(O)([O-])=O REULQIKBNNDNDX-UHFFFAOYSA-M 0.000 description 3
• 125000000542 sulfonic acid group Chemical group 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• 239000011573 trace mineral Substances 0.000 description 3
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• 239000001993 wax Substances 0.000 description 3
• DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 2
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