JPH0261921B2 - - Google Patents

Info

Publication number

JPH0261921B2

JPH0261921B2 JP57218466A JP21846682A JPH0261921B2 JP H0261921 B2 JPH0261921 B2 JP H0261921B2 JP 57218466 A JP57218466 A JP 57218466A JP 21846682 A JP21846682 A JP 21846682A JP H0261921 B2 JPH0261921 B2 JP H0261921B2

Authority

JP

Japan

Prior art keywords

eugenol

acetyl

choleretic

acetyl eugenol

results

Prior art date

1982-12-15

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 - Lifetime

Links

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• RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 52
• SCCDQYPEOIRVGX-UHFFFAOYSA-N Acetyleugenol Chemical compound COC1=CC(CC=C)=CC=C1OC(C)=O SCCDQYPEOIRVGX-UHFFFAOYSA-N 0.000 claims description 47
• NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 26
• 239000005770 Eugenol Substances 0.000 claims description 26
• UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 26
• 229960002217 eugenol Drugs 0.000 claims description 26
• 239000000731 choleretic agent Substances 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 3
• 230000001989 choleretic effect Effects 0.000 description 8
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 239000012230 colorless oil Substances 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• 239000002775 capsule Substances 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• FKJIJBSJQSMPTI-CAOXKPNISA-M sodium;(4r)-4-[(5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound [Na+].C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C FKJIJBSJQSMPTI-CAOXKPNISA-M 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• 210000000941 bile Anatomy 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• 230000000052 comparative effect Effects 0.000 description 2
• 238000000921 elemental analysis Methods 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 230000005484 gravity Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 238000000034 method Methods 0.000 description 2
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• 238000005303 weighing Methods 0.000 description 2
• 101710088194 Dehydrogenase Proteins 0.000 description 1
• 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 1
• 241001465754 Metazoa Species 0.000 description 1
• 241000219926 Myrtaceae Species 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 241000700157 Rattus norvegicus Species 0.000 description 1
• 244000223014 Syzygium aromaticum Species 0.000 description 1
• 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
• 210000001015 abdomen Anatomy 0.000 description 1
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
• 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
• 238000011047 acute toxicity test Methods 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 210000000013 bile duct Anatomy 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 231100000517 death Toxicity 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 239000007902 hard capsule Substances 0.000 description 1
• 241000411851 herbal medicine Species 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 230000005923 long-lasting effect Effects 0.000 description 1
• 231100000956 nontoxicity Toxicity 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• -1 polyethylene Polymers 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1