JPS6312052B2 - - Google Patents

Info

Publication number

JPS6312052B2

JPS6312052B2 JP2830180A JP2830180A JPS6312052B2 JP S6312052 B2 JPS6312052 B2 JP S6312052B2 JP 2830180 A JP2830180 A JP 2830180A JP 2830180 A JP2830180 A JP 2830180A JP S6312052 B2 JPS6312052 B2 JP S6312052B2

Authority

JP

Japan

Prior art keywords

acid

reaction

trimethoxybenzoic

tannic acid

present

Prior art date

1980-03-06

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

• Espacenet
• Global Dossier
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• SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 20
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 12
• 239000001263 FEMA 3042 Substances 0.000 claims description 12
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 12
• 235000015523 tannic acid Nutrition 0.000 claims description 12
• LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 12
• 229940033123 tannic acid Drugs 0.000 claims description 12
• 229920002258 tannic acid Polymers 0.000 claims description 12
• IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims description 10
• 238000006460 hydrolysis reaction Methods 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 238000007069 methylation reaction Methods 0.000 claims description 5
• 239000012022 methylating agents‎ Substances 0.000 claims description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 235000004515 gallic acid Nutrition 0.000 description 4
• 229940074391 gallic acid Drugs 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 230000003301 hydrolyzing effect Effects 0.000 description 3
• 239000000243 solution Substances 0.000 description 3
• 229920001864 tannin Polymers 0.000 description 3
• 235000018553 tannin Nutrition 0.000 description 3
• 239000001648 tannin Substances 0.000 description 3
• 238000010521 absorption reaction Methods 0.000 description 2
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
• 230000001035 methylating effect Effects 0.000 description 2
• 230000003472 neutralizing effect Effects 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• UHSXRTHJCJGEKG-UQKRIMTDSA-N (1s)-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-6,7-diol;chloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(C[C@H]2C3=CC(O)=C(O)C=C3CCN2)=C1 UHSXRTHJCJGEKG-UQKRIMTDSA-N 0.000 description 1
• HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
• 238000005481 NMR spectroscopy Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000011987 methylation Effects 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
• 229960001082 trimethoprim Drugs 0.000 description 1

Cited By (2)