CA1178958A - 2-substituted-phenyl-1,3-perhydrothiazine-4-one - Google Patents
2-substituted-phenyl-1,3-perhydrothiazine-4-oneInfo
- Publication number
- CA1178958A CA1178958A CA000387176A CA387176A CA1178958A CA 1178958 A CA1178958 A CA 1178958A CA 000387176 A CA000387176 A CA 000387176A CA 387176 A CA387176 A CA 387176A CA 1178958 A CA1178958 A CA 1178958A
- Authority
- CA
- Canada
- Prior art keywords
- group
- perhydrothiazine
- phenyl
- formula
- chemical equivalent
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 15
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 9
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 8
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 7
- 239000001099 ammonium carbonate Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- RNZPUDNTBZUVDK-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)-1,3-thiazinan-4-one Chemical compound COC1=C(OC)C(OC)=CC(C2SCCC(=O)N2)=C1 RNZPUDNTBZUVDK-UHFFFAOYSA-N 0.000 claims description 4
- HQOIEHGBVFDGJI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,3-thiazinan-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1SCCC(=O)N1 HQOIEHGBVFDGJI-UHFFFAOYSA-N 0.000 claims description 4
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 claims description 4
- 150000003868 ammonium compounds Chemical class 0.000 claims description 4
- JLSJEUQOXVVCPN-UHFFFAOYSA-N 3-sulfanylpropanamide Chemical compound NC(=O)CCS JLSJEUQOXVVCPN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CQULDBBHGMHIAE-UHFFFAOYSA-N 2-(2-methoxyphenyl)-1,3-thiazinan-4-one Chemical compound COC1=CC=CC=C1C1SCCC(=O)N1 CQULDBBHGMHIAE-UHFFFAOYSA-N 0.000 claims description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims 2
- 208000008469 Peptic Ulcer Diseases 0.000 abstract description 28
- 208000011906 peptic ulcer disease Diseases 0.000 abstract description 28
- 230000002467 anti-pepsin effect Effects 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 208000025865 Ulcer Diseases 0.000 description 19
- 239000003814 drug Substances 0.000 description 18
- 241000700159 Rattus Species 0.000 description 15
- 231100000397 ulcer Toxicity 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000011047 acute toxicity test Methods 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
- 238000011156 evaluation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012153 distilled water 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
- 239000002504 physiological saline solution Substances 0.000 description 3
- 230000000384 rearing effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000723 toxicological property Toxicity 0.000 description 3
- -1 troches Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 229920002261 Corn starch 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
- 210000003484 anatomy Anatomy 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 210000000467 autonomic pathway 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
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 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
- 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
- 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
- 210000001187 pylorus Anatomy 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000002562 urinalysis Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-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
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-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
- 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
- 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
- 230000001154 acute effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000000903 blocking effect Effects 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
- 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000002496 gastric effect Effects 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
- 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
- 125000002887 hydroxy group Chemical group [H]O* 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
- 239000008101 lactose Substances 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 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
- 230000003340 mental effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose 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
- 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
- 230000001175 peptic 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
- 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
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 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
- 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
- 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 238000005303 weighing Methods 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP141240/80 | 1980-10-09 | ||
| JP55141240A JPS5764685A (en) | 1980-10-09 | 1980-10-09 | 2-(substituted phenyl)-1,3-thiazin-4(3,5,6h)-one and remedy for peptic ulcer containing said compound as active component |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1178958A true CA1178958A (en) | 1984-12-04 |
Family
ID=15287350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000387176A Expired CA1178958A (en) | 1980-10-09 | 1981-10-02 | 2-substituted-phenyl-1,3-perhydrothiazine-4-one |
Country Status (7)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004538285A (ja) * | 2001-07-16 | 2004-12-24 | ユーロ−セルティック エス． ア． | アリール置換チアゾリジノンおよびその使用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA624416A (en) * | 1961-07-25 | R. Surrey Alexander | 2-aryl-4-metathiazanones and derivatives | |
| US3082209A (en) * | 1958-11-28 | 1963-03-19 | Sterling Drug Inc | 4-metathiazanone derivatives and their preparation |
| CA1154447A (en) | 1979-07-09 | 1983-09-27 | Takao Kawasaki | 2-substituted-4-thiazolidones |
-
1980
- 1980-10-09 JP JP55141240A patent/JPS5764685A/ja active Granted
-
1981
- 1981-10-02 CA CA000387176A patent/CA1178958A/en not_active Expired
- 1981-10-07 DE DE8181304654T patent/DE3165695D1/de not_active Expired
- 1981-10-07 EP EP81304654A patent/EP0050003B1/en not_active Expired
- 1981-10-07 US US06/309,187 patent/US4407799A/en not_active Expired - Lifetime
- 1981-10-08 KR KR1019810003808A patent/KR860000060B1/ko not_active Expired
- 1981-10-09 ES ES506701A patent/ES506701A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3165695D1 (en) | 1984-09-27 |
| ES8303381A1 (es) | 1983-02-01 |
| JPS6310951B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-10 |
| EP0050003A1 (en) | 1982-04-21 |
| KR830007605A (ko) | 1983-11-04 |
| EP0050003B1 (en) | 1984-08-22 |
| KR860000060B1 (ko) | 1986-02-06 |
| JPS5764685A (en) | 1982-04-19 |
| US4407799A (en) | 1983-10-04 |
| ES506701A0 (es) | 1983-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4558059A (en) | 2-Substituted-phenylthiazole derivatives | |
| US4567179A (en) | Antiinflammatory salts of piroxicam | |
| AU629322B2 (en) | Aryl-substituted rhodanine derivatives | |
| US4363813A (en) | 2-(3,4,5-Trimethoxyphenyl)-4,5-disubstituted thiazoles | |
| US4434172A (en) | 2-Substituted-phenyl-5-alkylthiazolidine-4-one | |
| US4337259A (en) | Pyridine derivatives | |
| CA1178958A (en) | 2-substituted-phenyl-1,3-perhydrothiazine-4-one | |
| US4722932A (en) | 2-substituted-4-thiazolidones | |
| US5004742A (en) | Benzothiazine-1,1-dioxide derivatives | |
| US4297357A (en) | N-Phenethylacetamide compounds and process for preparation thereof | |
| JP2002515042A (ja) | 糖尿病、異常脂血症（ｄｙｓｌｉｐｉｄｅｍｉａ）および高血圧の治療に有用なアゾリジンジオン（ａｚｏｌｉｄｉｎｅｄｉｏｎｅ）およびそれらを含有する組成物 | |
| CA1332419C (en) | 2-thiazolidinone derivatives, pharmaceutical compositions containing them and process for preparing same | |
| US4267189A (en) | Method of use and composition for 1,3-dihydro-3-(2-hydroxy-2-methylpropyl)-2H-isoindol-1-one | |
| US4126625A (en) | Certain 5-substituted-3-methyl-2-benzofuran acetic acids | |
| JPS6310949B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0404949A1 (en) | Substituted acetamide derivatives, process for their preparation and antiulcer drug containing same | |
| HU196584B (en) | Process for producing 4-phenyl-2-oxo-2-butenoic acid derivatives and pharmaceutics comprising such active ingredient | |
| US4415579A (en) | Pyridine derivatives | |
| KR840002072B1 (ko) | 2-치환-4-티아졸리돈의 제조방법 | |
| US4172145A (en) | Benzo(b)furylacetic acid derivatives to reduce inflammation | |
| JPS6330462A (ja) | 新規グアニジノメチルベンツアミド誘導体およびそれを有効成分とする抗潰瘍剤 | |
| JPS6310950B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS6151580B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4143148A (en) | Anti-ulcer thiazoline derivatives | |
| CA1306464C (en) | 2-(3, 5-dimethyl-4-hydroxyphenyl)indole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |