JPS6310701B2 - - Google Patents
Info
- Publication number
- JPS6310701B2 JPS6310701B2 JP8705579A JP8705579A JPS6310701B2 JP S6310701 B2 JPS6310701 B2 JP S6310701B2 JP 8705579 A JP8705579 A JP 8705579A JP 8705579 A JP8705579 A JP 8705579A JP S6310701 B2 JPS6310701 B2 JP S6310701B2
- Authority
- JP
- Japan
- Prior art keywords
- ulcer
- formula
- compound
- acetylthiazole
- trimethoxyphenyl
- 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
- 238000000034 method Methods 0.000 claims description 13
- 239000003699 antiulcer agent Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- FCQGHVXXICVSIF-UHFFFAOYSA-N 3,4,5-trimethoxybenzenecarbothioamide Chemical compound COC1=CC(C(N)=S)=CC(OC)=C1OC FCQGHVXXICVSIF-UHFFFAOYSA-N 0.000 claims description 5
- GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 claims description 4
- 230000002467 anti-pepsin effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- HYMSODFAXMRQCU-UHFFFAOYSA-N 1-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazol-5-yl]ethanone Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(C)=O)=C1 HYMSODFAXMRQCU-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 208000025865 Ulcer Diseases 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- 231100000397 ulcer Toxicity 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 239000013078 crystal Substances 0.000 description 5
- 208000008469 Peptic Ulcer Diseases 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 210000001187 pylorus Anatomy 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000007979 thiazole derivatives Chemical class 0.000 description 3
- ASYBEJAJVKOXLG-UHFFFAOYSA-N 1-chloropentane-2,4-dione Chemical compound CC(=O)CC(=O)CCl ASYBEJAJVKOXLG-UHFFFAOYSA-N 0.000 description 2
- -1 4-methyl-5-acetylthiazole 3,4,5-trimethoxythiobenzamide Chemical compound 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 208000011906 peptic ulcer disease Diseases 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- BTJMOXDWIPVCRO-UHFFFAOYSA-N 2,3,4-trimethoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C(OC)=C1OC BTJMOXDWIPVCRO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000031648 Body Weight Changes Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 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
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 210000000467 autonomic pathway Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000010876 biochemical test Methods 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 230000004579 body weight change Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 235000021050 feed intake Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000000712 neurohormone Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940095353 oral granules Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8705579A JPS5612377A (en) | 1979-07-09 | 1979-07-09 | Novel thiazole derivative, its preparation, and drug for ulcer having andigestive action |
| US06/163,507 US4363813A (en) | 1979-07-09 | 1980-06-27 | 2-(3,4,5-Trimethoxyphenyl)-4,5-disubstituted thiazoles |
| CA000355635A CA1150272A (en) | 1979-07-09 | 1980-07-07 | 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles |
| GB8022292A GB2056440B (en) | 1979-07-09 | 1980-07-08 | 2 - (3,4,5 - trimethoxyphenyl)thiazoles |
| IT23315/80A IT1131682B (it) | 1979-07-09 | 1980-07-08 | 2-(3,4,5-trimetossifenil)-tiazoli 4,5-bisostituiti e procedimento per la loro preparazione |
| FR8015210A FR2465729A1 (fr) | 1979-07-09 | 1980-07-08 | 2-(3,4,5-trimethoxyphenyl)-thiazoles substitues, medicaments les contenant et procede pour leur fabrication |
| DE3026054A DE3026054C2 (de) | 1979-07-09 | 1980-07-09 | 4,5-disubstituierte2-(3,4,5-Trimethoxyphenyl)-thiazole und dieselben enthaltendes Mittel |
| ES493650A ES8105987A1 (es) | 1979-07-09 | 1980-07-09 | Procedimiento para la fabricacion de 2(3,4,5-trimetoxifenil)tiazoles,4,5-disubstituidos |
| ES500076A ES8201565A1 (es) | 1979-07-09 | 1981-02-13 | Metodo perfeccionado para la fabricacion de 2-(3,4,5-trime- toxifenil),4,5-disubstituidos |
| CA000417020A CA1158247A (en) | 1979-07-09 | 1982-12-03 | 2,(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8705579A JPS5612377A (en) | 1979-07-09 | 1979-07-09 | Novel thiazole derivative, its preparation, and drug for ulcer having andigestive action |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5612377A JPS5612377A (en) | 1981-02-06 |
| JPS6310701B2 true JPS6310701B2 (ru) | 1988-03-08 |
Family
ID=13904248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8705579A Granted JPS5612377A (en) | 1979-07-09 | 1979-07-09 | Novel thiazole derivative, its preparation, and drug for ulcer having andigestive action |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5612377A (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05111107A (ja) * | 1991-10-18 | 1993-04-30 | Hitachi Cable Ltd | 絶縁トロリー用集電装置 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59106170U (ja) * | 1983-01-07 | 1984-07-17 | 日本電気株式会社 | 平面形表示管を用いた装置 |
| GB8302591D0 (en) * | 1983-01-31 | 1983-03-02 | Fujisawa Pharmaceutical Co | Thiazole derivatives |
| JPH0679750B2 (ja) * | 1987-02-20 | 1994-10-12 | 株式会社板屋製作所 | バネ製造装置及びその方法 |
| JPH0321786Y2 (ru) * | 1987-03-20 | 1991-05-13 | ||
| JPH0321787Y2 (ru) * | 1987-03-20 | 1991-05-13 | ||
| JP2508071Y2 (ja) * | 1989-06-22 | 1996-08-21 | 旭精機工業株式会社 | コイルばね製造機の自由長調整装置 |
-
1979
- 1979-07-09 JP JP8705579A patent/JPS5612377A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05111107A (ja) * | 1991-10-18 | 1993-04-30 | Hitachi Cable Ltd | 絶縁トロリー用集電装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5612377A (en) | 1981-02-06 |
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