CA1163636A - 2-substituted-phenylthiazole derivatives - Google Patents
2-substituted-phenylthiazole derivativesInfo
- Publication number
- CA1163636A CA1163636A CA000388313A CA388313A CA1163636A CA 1163636 A CA1163636 A CA 1163636A CA 000388313 A CA000388313 A CA 000388313A CA 388313 A CA388313 A CA 388313A CA 1163636 A CA1163636 A CA 1163636A
- Authority
- CA
- Canada
- Prior art keywords
- methylthiazole
- methoxyphenyl
- derivative
- hydrogen atom
- lower alkyl
- 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 2-substituted-phenylthiazole Chemical class 0.000 title claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 26
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000005915 ammonolysis reaction Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- JFSYHABOGPOERA-UHFFFAOYSA-N ethyl 2-(2-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C(=CC=CC=2)OC)=N1 JFSYHABOGPOERA-UHFFFAOYSA-N 0.000 claims description 4
- OYDTZYBFGUQOJX-UHFFFAOYSA-N ethyl 2-(3,4-dimethoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C=C(OC)C(OC)=CC=2)=N1 OYDTZYBFGUQOJX-UHFFFAOYSA-N 0.000 claims description 4
- JSRLIKYMFUPJKF-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C=CC(OC)=CC=2)=N1 JSRLIKYMFUPJKF-UHFFFAOYSA-N 0.000 claims description 4
- KUUQMVAMUVEWCA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C)=C(C(N)=O)S1 KUUQMVAMUVEWCA-UHFFFAOYSA-N 0.000 claims description 3
- GPLLJBLZFRBIEX-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC)SC(C=2C=CC(OC)=CC=2)=N1 GPLLJBLZFRBIEX-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- ODXUWYRAHXUBLC-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC(C)=C(C(N)=O)S1 ODXUWYRAHXUBLC-UHFFFAOYSA-N 0.000 claims 2
- QNIHAJJHPNMVJY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC)SC(C=2C=C(OC)C(OC)=CC=2)=N1 QNIHAJJHPNMVJY-UHFFFAOYSA-N 0.000 claims 1
- POBBOXLBMOZSGR-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)-4-methyl-1,3-thiazol-5-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=NC(C)=C(CC(N)=O)S1 POBBOXLBMOZSGR-UHFFFAOYSA-N 0.000 claims 1
- 230000011514 reflex Effects 0.000 claims 1
- 208000008469 Peptic Ulcer Diseases 0.000 abstract description 30
- 208000011906 peptic ulcer disease Diseases 0.000 abstract description 30
- 230000002467 anti-pepsin effect Effects 0.000 abstract description 19
- 230000000694 effects Effects 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 description 39
- 208000025865 Ulcer Diseases 0.000 description 22
- 239000003814 drug Substances 0.000 description 20
- 241000700159 Rattus Species 0.000 description 16
- 231100000397 ulcer Toxicity 0.000 description 15
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000000384 rearing effect Effects 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000723 toxicological property Toxicity 0.000 description 3
- GGNMTJKRHHLJHH-UHFFFAOYSA-N 3,4,5-trimethoxybenzamide Chemical compound COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 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 2
- 229920001386 Gefarnate Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 238000011047 acute toxicity test Methods 0.000 description 2
- 210000003484 anatomy Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 230000002183 duodenal effect Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229960003779 gefarnate Drugs 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
- 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
- 210000000056 organ Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- 238000002562 urinalysis 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
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- GEXIUKNFKXMXHI-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC(C)=C(C(N)=O)S1 GEXIUKNFKXMXHI-UHFFFAOYSA-N 0.000 description 1
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 description 1
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-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
- 244000215068 Acacia senegal Species 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
- 229920000945 Amylopectin Polymers 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010020772 Hypertension 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
- 208000006550 Mydriasis Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 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
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 210000000467 autonomic pathway Anatomy 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 239000006172 buffering agent 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
- 239000002775 capsule Substances 0.000 description 1
- 229960000530 carbenoxolone Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 230000009982 effect on human Effects 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
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 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
- 230000036407 pain Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 210000005037 parasympathetic nerve Anatomy 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940111202 pepsin Drugs 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
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000013641 positive control Substances 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
- 238000010298 pulverizing process Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP149200/80 | 1980-10-24 | ||
| JP55149200A JPS5772975A (en) | 1980-10-24 | 1980-10-24 | 2-substituted phenylthiazole derviative, and medicine for peptic ulcer containing said derivative as active component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163636A true CA1163636A (en) | 1984-03-13 |
Family
ID=15470005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000388313A Expired CA1163636A (en) | 1980-10-24 | 1981-10-20 | 2-substituted-phenylthiazole derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4558059A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0051409B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5772975A (cg-RX-API-DMAC7.html) |
| KR (1) | KR850001933B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1163636A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3162824D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES8303375A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4879295A (en) * | 1986-09-27 | 1989-11-07 | Sawai Pharmaceutical Co., Ltd. | N-tetrazolyl thiazolecarboxyamide derivatives and their use |
| EP0321115B1 (en) * | 1987-12-14 | 1991-08-14 | Sawai Pharmaceutical Co., Ltd. | Carboxamide derivatives having tetrazole and thiazole rings and their use |
| DK0513379T3 (da) * | 1990-11-30 | 1996-09-30 | Teijin Ltd | 2-Arylthiazolderivater og farmaceutisk præparat indeholdende sådanne |
| US6083966A (en) * | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| WO2000016763A2 (en) * | 1998-09-21 | 2000-03-30 | University Of Florida Research Foundation, Inc. | Antimalarial agents |
| WO2004017959A2 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| WO2005034949A1 (en) * | 2003-09-09 | 2005-04-21 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| EP1866296B1 (en) | 2005-04-04 | 2016-11-02 | University of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
| NZ579994A (en) * | 2007-03-15 | 2011-09-30 | Univ Florida | Desferrithiocin polyether analogues useful in the treatment of pathological conditions responsive to chelation or sequestration of trivalent metal |
| KR102111176B1 (ko) | 2011-12-16 | 2020-05-15 | 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 | 4'-데스페리티오신 유사체의 용도 |
| AU2014352780A1 (en) | 2013-11-22 | 2016-06-09 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogs and uses thereof |
| WO2016176343A1 (en) | 2015-04-27 | 2016-11-03 | University Of Florida Research Foundation, Incorporated | Metabolically programmed metal chelators and uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1546183A (fr) * | 1966-12-07 | 1968-11-15 | Uniroyal Inc | Carboxamidothiazoles, leurs substituants et dérivés, leurs procédés de fabrication ainsi que leurs applications et procédés d'application agriculturaux |
| US3794636A (en) * | 1971-09-03 | 1974-02-26 | Uniroyal Ltd | Process for preparation of thiazole hydrohalides |
| US4199506A (en) * | 1978-05-15 | 1980-04-22 | Monsanto Company | 2,4-Disubstituted-5-thiazolecarboxylic acids and derivatives |
| US4336389A (en) * | 1978-05-15 | 1982-06-22 | Monsanto Company | 2-Substituted-4-aryl-5-thiazolecarboxylic acids and their derivatives as safening agents |
| US4363813A (en) * | 1979-07-09 | 1982-12-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | 2-(3,4,5-Trimethoxyphenyl)-4,5-disubstituted thiazoles |
| JPS5657776A (en) * | 1979-10-17 | 1981-05-20 | Kumiai Chem Ind Co Ltd | Thiazole derivative and fungicide comprising it |
-
1980
- 1980-10-24 JP JP55149200A patent/JPS5772975A/ja active Granted
-
1981
- 1981-10-20 ES ES507001A patent/ES8303375A1/es not_active Expired
- 1981-10-20 CA CA000388313A patent/CA1163636A/en not_active Expired
- 1981-10-23 EP EP81305012A patent/EP0051409B1/en not_active Expired
- 1981-10-23 DE DE8181305012T patent/DE3162824D1/de not_active Expired
- 1981-10-24 KR KR1019810004046A patent/KR850001933B1/ko not_active Expired
-
1984
- 1984-11-14 US US06/671,067 patent/US4558059A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES507001A0 (es) | 1983-02-01 |
| KR850001933B1 (ko) | 1985-12-31 |
| US4558059A (en) | 1985-12-10 |
| JPS5772975A (en) | 1982-05-07 |
| ES8303375A1 (es) | 1983-02-01 |
| EP0051409A1 (en) | 1982-05-12 |
| JPS6148834B2 (cg-RX-API-DMAC7.html) | 1986-10-25 |
| EP0051409B1 (en) | 1984-03-21 |
| DE3162824D1 (en) | 1984-04-26 |
| KR830007603A (ko) | 1983-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1163636A (en) | 2-substituted-phenylthiazole derivatives | |
| US4567179A (en) | Antiinflammatory salts of piroxicam | |
| CA1150272A (en) | 2-(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles | |
| EP0033617A2 (en) | Thiazolidine derivatives and their production and medicinal compositions containing them | |
| JPWO1998017654A1 (ja) | 置換ベンゾイルアミノチアゾール誘導体及びそれを含有する医薬 | |
| US4337259A (en) | Pyridine derivatives | |
| JPS6348873B2 (cg-RX-API-DMAC7.html) | ||
| US4434172A (en) | 2-Substituted-phenyl-5-alkylthiazolidine-4-one | |
| EP0413051B1 (en) | Benzothiazine-1,1-dioxide derivatives | |
| EP0050003B1 (en) | 2-(substituted phenyl)-1,3-perhydrothiazine-4-ones for treating peptic ulcers | |
| US4722932A (en) | 2-substituted-4-thiazolidones | |
| JPS6310701B2 (cg-RX-API-DMAC7.html) | ||
| US4126625A (en) | Certain 5-substituted-3-methyl-2-benzofuran acetic acids | |
| DD154608A5 (de) | Verfahren zur herstellung von 1x oxo-1h-thiazolo-[3,2-a]pyrimidin-carboxamiden u.deren zwischenstufen | |
| GB2069493A (en) | Pyridine derivatives | |
| CA1158247A (en) | 2,(3,4,5-trimethoxyphenyl)-4,5-disubstituted thiazoles | |
| US4267189A (en) | Method of use and composition for 1,3-dihydro-3-(2-hydroxy-2-methylpropyl)-2H-isoindol-1-one | |
| US4172145A (en) | Benzo(b)furylacetic acid derivatives to reduce inflammation | |
| KR840001932B1 (ko) | 2-(3,4,5-트리메톡시페닐)-4,5-이치환된 티아졸의 제조방법 | |
| US4415579A (en) | Pyridine derivatives | |
| EP0178822B1 (en) | 2-guanidino-4-(2-methyl-4-imidazolyl)thiazoles in the treatment of rheumatoid arthritis | |
| JPS6310949B2 (cg-RX-API-DMAC7.html) | ||
| JPS6310950B2 (cg-RX-API-DMAC7.html) | ||
| KR840002072B1 (ko) | 2-치환-4-티아졸리돈의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |