CA1158247A - 2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles - Google Patents

2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles

Info

Publication number: CA1158247A
Authority: CA; Canada
Prior art keywords: group; trimethoxyphenyl; compound; peptic ulcer; ulcer
Prior art date: 1979-07-09
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

Application number

CA000417020A

Other languages

English (en)

Inventor

Takao Kawasaki

Yoshiaki Osaka

Tadashi Tsuchiya

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kureha Corp

Original Assignee

Kureha Corp

Priority date (The priority date 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 date listed.)

1979-07-09

Filing date

1982-12-03

Publication date

1983-12-06

1979-07-09 Priority claimed from JP8705579A external-priority patent/JPS5612377A/ja

1980-05-23 Priority claimed from JP6850780A external-priority patent/JPS56164175A/ja

1980-07-07 Priority claimed from CA000355635A external-priority patent/CA1150272A/fr

1982-12-03 Application filed by Kureha Corp filed Critical Kureha Corp

1982-12-03 Priority to CA000417020A priority Critical patent/CA1158247A/fr

1983-12-06 Application granted granted Critical

1983-12-06 Publication of CA1158247A publication Critical patent/CA1158247A/fr

Status Expired legal-status Critical Current

Links

150000003557 thiazoles Chemical class 0.000 title abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 26
-1 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
208000008469 Peptic Ulcer Diseases 0.000 abstract description 37
208000011906 peptic ulcer disease Diseases 0.000 abstract description 36
230000002467 anti-pepsin effect Effects 0.000 abstract description 19
230000000694 effects Effects 0.000 abstract description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
238000009833 condensation Methods 0.000 abstract description 2
230000005494 condensation Effects 0.000 abstract description 2
238000007363 ring formation reaction Methods 0.000 abstract description 2
239000000243 solution Substances 0.000 description 23
241000700159 Rattus Species 0.000 description 20
208000025865 Ulcer Diseases 0.000 description 18
239000013078 crystal Substances 0.000 description 18
231100000397 ulcer Toxicity 0.000 description 18
239000003814 drug Substances 0.000 description 17
239000000203 mixture Substances 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
239000000047 product Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 10
ZPACYDRSPFRDHO-ROBAGEODSA-N Gefarnate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(=O)OC\C=C(/C)CCC=C(C)C ZPACYDRSPFRDHO-ROBAGEODSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
230000000875 corresponding effect Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
229920001386 Gefarnate Polymers 0.000 description 6
229960003779 gefarnate Drugs 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
230000001629 suppression Effects 0.000 description 5
238000012360 testing method Methods 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
230000037396 body weight Effects 0.000 description 4
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 4
238000012216 screening Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000010171 animal model Methods 0.000 description 3
238000011888 autopsy Methods 0.000 description 3
235000005911 diet Nutrition 0.000 description 3
230000037213 diet Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
210000001187 pylorus Anatomy 0.000 description 3
238000010189 synthetic method Methods 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
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 description 2
KBXUOHZHHFXVDI-UHFFFAOYSA-N 2,3,4-trimethoxybenzenecarbothioamide Chemical compound COC1=CC=C(C(N)=S)C(OC)=C1OC KBXUOHZHHFXVDI-UHFFFAOYSA-N 0.000 description 2
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical compound CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 2
GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
FCQGHVXXICVSIF-UHFFFAOYSA-N 3,4,5-trimethoxybenzenecarbothioamide Chemical compound COC1=CC(C(N)=S)=CC(OC)=C1OC FCQGHVXXICVSIF-UHFFFAOYSA-N 0.000 description 2
RJAHEEXALIVZOV-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(O)=O)=C1 RJAHEEXALIVZOV-UHFFFAOYSA-N 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000011047 acute toxicity test Methods 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
239000003699 antiulcer agent Substances 0.000 description 2
210000001198 duodenum Anatomy 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
230000000384 rearing effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
231100000161 signs of toxicity Toxicity 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000002110 toxicologic effect Effects 0.000 description 2
VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 description 1
YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 description 1
MRPPJNNNALBORN-UHFFFAOYSA-N 2,3,4-trimethoxythiobenzaldehyde Chemical compound COC1=CC=C(C=S)C(OC)=C1OC MRPPJNNNALBORN-UHFFFAOYSA-N 0.000 description 1
ABCRJWMADDBQFJ-UHFFFAOYSA-N 2-chloropentan-3-one Chemical compound CCC(=O)C(C)Cl ABCRJWMADDBQFJ-UHFFFAOYSA-N 0.000 description 1
RVLGQEAHODLXFL-UHFFFAOYSA-N 4-ethyl-5-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole Chemical compound S1C(C)=C(CC)N=C1C1=CC(OC)=C(OC)C(OC)=C1 RVLGQEAHODLXFL-UHFFFAOYSA-N 0.000 description 1
ZGWGSEUMABQEMD-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=CSC=1C(O)=O ZGWGSEUMABQEMD-UHFFFAOYSA-N 0.000 description 1
ZTOXCZMCCDLXAA-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole Chemical compound COC1=C(OC)C(OC)=CC(C=2SC=C(C)N=2)=C1 ZTOXCZMCCDLXAA-UHFFFAOYSA-N 0.000 description 1
FGWYAVBTEVOOSJ-UHFFFAOYSA-N 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-5-carbohydrazide Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(=O)NN)=C1 FGWYAVBTEVOOSJ-UHFFFAOYSA-N 0.000 description 1
VOKDWPMRYSKGTB-UHFFFAOYSA-N 5,9,13-trimethyltetradeca-4,8,12-trienoic acid Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC(O)=O VOKDWPMRYSKGTB-UHFFFAOYSA-N 0.000 description 1
UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000586542 Aonidiella citrina Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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 1
239000004150 EU approved colour Substances 0.000 description 1
206010060891 General symptom Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
206010020601 Hyperchlorhydria Diseases 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
229930195725 Mannitol Natural products 0.000 description 1
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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 1
229930006000 Sucrose Natural products 0.000 description 1
QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
OVYZSBXTDTZISH-UHFFFAOYSA-N acetic acid N-[1-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazol-5-yl]ethylidene]hydroxylamine Chemical compound C(C)(=O)O.COC=1C=C(C=C(C1OC)OC)C=1SC(=C(N1)C)C(C)=NO OVYZSBXTDTZISH-UHFFFAOYSA-N 0.000 description 1
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 1
230000002378 acidificating effect Effects 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229960001231 choline Drugs 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
XUCARBXWGUJVRR-UHFFFAOYSA-N ethyl 3-(2-oxopropyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(CC(C)=O)=C1 XUCARBXWGUJVRR-UHFFFAOYSA-N 0.000 description 1
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
ATYLSULJZJFGSN-UHFFFAOYSA-N ethyl 4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C=C(OC)C(OC)=C(OC)C=2)=N1 ATYLSULJZJFGSN-UHFFFAOYSA-N 0.000 description 1
235000021050 feed intake Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000035876 healing Effects 0.000 description 1
210000002216 heart Anatomy 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
101150085091 lat-2 gene Proteins 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
RFJOPLSPHYCBOZ-UHFFFAOYSA-N n-[1-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-thiazol-5-yl]ethylidene]hydroxylamine Chemical compound COC1=C(OC)C(OC)=CC(C=2SC(=C(C)N=2)C(C)=NO)=C1 RFJOPLSPHYCBOZ-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
101150096078 outD gene Proteins 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000723 toxicological property Toxicity 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
238000002562 urinalysis Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000417020A 1979-07-09 1982-12-03 2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles Expired CA1158247A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000417020A CA1158247A (fr)	1979-07-09	1982-12-03	2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles

Applications Claiming Priority (6)

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
JP87055/79		1979-07-09
JP6850780A JPS56164175A (en)	1980-05-23	1980-05-23	Novel thiazole derivative and antipeptic ulcer agent containing the same as active constituent
JP68507/80		1980-05-23
CA000355635A CA1150272A (fr)	1979-07-09	1980-07-07	2-(3,4,5-trimethoxyphenyl) thiazoles substitues en 4 et 5
CA000417020A CA1158247A (fr)	1979-07-09	1982-12-03	2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles

Publications (1)

Publication Number	Publication Date
CA1158247A true CA1158247A (fr)	1983-12-06

Family

ID=27426249

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000417020A Expired CA1158247A (fr)	1979-07-09	1982-12-03	2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles

Country Status (1)

Country	Link
CA (1)	CA1158247A (fr)

1982
- 1982-12-03 CA CA000417020A patent/CA1158247A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-12-06	MKEX	Expiry

Publication	Publication Date	Title
CA1150272A (fr)	1983-07-19	2-(3,4,5-trimethoxyphenyl) thiazoles substitues en 4 et 5
JPS61286376A (ja)	1986-12-16	チアゾリジン誘導体およびそれを含んでなる医薬組成物
US4558059A (en)	1985-12-10	2-Substituted-phenylthiazole derivatives
US3332942A (en)	1967-07-25	Substituted thiadiazoles
JPS6348873B2 (fr)	1988-09-30
CA1158247A (fr)	1983-12-06	2,(3,4,5-trimethoxyphenyl)-4,5-disubstituant thiazoles
CA1128517A (fr)	1982-07-27	Disulfures
US4540702A (en)	1985-09-10	2-Substituted-4-thiazolidones
US4434172A (en)	1984-02-28	2-Substituted-phenyl-5-alkylthiazolidine-4-one
FR2503713A1 (fr)	1982-10-15	2,3-di-substitue-5,6-dihydro-imidazo-(2,1-b) thiazoles, procede pour leur preparation et agents anti-inflammatoires les contenant
HU214337B (hu)	1998-03-02	Eljárás 1,3,4-tiadiazin-2-on-származékok és az azokat tartalmazó gyógyszer készítmények előállítására
US4137320A (en)	1979-01-30	Pharmaceutical compositions containing imidazo(2,1-b)thiazoles and process for reducing blood sugar levels therewith
KR840001932B1 (ko)	1984-10-25	2-(3,4,5-트리메톡시페닐)-4,5-이치환된 티아졸의 제조방법
NL8006362A (nl)	1981-06-16	Anti-allergische en antimaagzweer 1-oxo-1 h- -thiazolo/3,2-a/ pyrimidine-2-carbonamiden en tussenprodukten daarvoor.
JPS6310950B2 (fr)	1988-03-10
EP0050003B1 (fr)	1984-08-22	(Phényle substitué)2-perhydrothiazin-1,3-ones-4 et leur emploi pour le traitement d'ulcères
AU665285B2 (en)	1995-12-21	New 4-methyl-1, 3-oxazole compounds, process for preparing them and pharmaceutical compositions containing them
JP2678768B2 (ja)	1997-11-17	テトラヒドロイミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤
JPS60231667A (ja)	1985-11-18	ベンゾチアゾール誘導体、その製造方法および医薬組成物
EP0178822B1 (fr)	1990-01-17	2-Guanidino-4-(2-méthyl-4-imidazolyl)-thiazoles dans le traitement de l'arthrite rhumatoide
JP2535533B2 (ja)	1996-09-18	ベンゾジオキソ−ル誘導体
JPH0440356B2 (fr)	1992-07-02
IL45147A (en)	1977-05-31	2,5-bis-substituted amino-1,3,4-thiadiazoles and method of preparation
KR840002072B1 (ko)	1984-11-09	2-치환-4-티아졸리돈의 제조방법
JPS6310949B2 (fr)	1988-03-10