JPS6115060B2 - - Google Patents
Info
- Publication number
- JPS6115060B2 JPS6115060B2 JP8780977A JP8780977A JPS6115060B2 JP S6115060 B2 JPS6115060 B2 JP S6115060B2 JP 8780977 A JP8780977 A JP 8780977A JP 8780977 A JP8780977 A JP 8780977A JP S6115060 B2 JPS6115060 B2 JP S6115060B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- butenyloxy
- group
- carboxymethoxy
- ethanol
- Prior art date
- 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
- -1 3-methyl-2-butenyloxy group Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001788 chalcone derivatives Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
- 239000000203 mixture Substances 0.000 description 10
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 235000005513 chalcones Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- JDBCUMHVIOQAAR-UHFFFAOYSA-N 3-(3-methylbut-2-enoxy)benzaldehyde Chemical compound CC(C)=CCOC1=CC=CC(C=O)=C1 JDBCUMHVIOQAAR-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 210000001015 abdomen Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- HMBNSDWJNMBKAE-UHFFFAOYSA-N ethyl 2-(3-formylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC(C=O)=C1 HMBNSDWJNMBKAE-UHFFFAOYSA-N 0.000 description 3
- 210000001187 pylorus Anatomy 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000002467 anti-pepsin effect Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 208000011906 peptic ulcer disease Diseases 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- NGQJIEUOZYTRPF-UHFFFAOYSA-N 3-[2-(3-methylbuta-1,3-dienyl)phenyl]-1-phenylprop-2-en-1-one Chemical compound CC(=C)C=CC1=CC=CC=C1C=CC(=O)C1=CC=CC=C1 NGQJIEUOZYTRPF-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- YVWJJQUUORDFCC-UHFFFAOYSA-N ethyl 2-(2-formylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C=O YVWJJQUUORDFCC-UHFFFAOYSA-N 0.000 description 1
- FEUFLYNZOILPFG-UHFFFAOYSA-N ethyl 2-phenacyloxyacetate Chemical compound CCOC(=O)COCC(=O)C1=CC=CC=C1 FEUFLYNZOILPFG-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8780977A JPS5422349A (en) | 1977-07-21 | 1977-07-21 | Chalcone compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8780977A JPS5422349A (en) | 1977-07-21 | 1977-07-21 | Chalcone compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5422349A JPS5422349A (en) | 1979-02-20 |
| JPS6115060B2 true JPS6115060B2 (ko) | 1986-04-22 |
Family
ID=13925295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8780977A Granted JPS5422349A (en) | 1977-07-21 | 1977-07-21 | Chalcone compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5422349A (ko) |
-
1977
- 1977-07-21 JP JP8780977A patent/JPS5422349A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5422349A (en) | 1979-02-20 |
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