DE2537070C2 - - Google Patents
Info
- Publication number
- DE2537070C2 DE2537070C2 DE2537070A DE2537070A DE2537070C2 DE 2537070 C2 DE2537070 C2 DE 2537070C2 DE 2537070 A DE2537070 A DE 2537070A DE 2537070 A DE2537070 A DE 2537070A DE 2537070 C2 DE2537070 C2 DE 2537070C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- carboxylic acid
- hydroxy
- thiophene
- methyl
- 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 description 55
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- -1 2-thiazolyl Chemical group 0.000 claims description 11
- MAURGJMKVGWXMC-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)thieno[2,3-e]thiazine-3-carboxamide Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 MAURGJMKVGWXMC-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- TZIJDLHRFZUDHD-UHFFFAOYSA-N 2h-thieno[2,3-e]thiazine Chemical class C1=CNSC2=C1SC=C2 TZIJDLHRFZUDHD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- FLUWHUVICKOETA-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)thieno[3,4-e]thiazine-3-carboxamide Chemical compound OC=1C2=CSC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 FLUWHUVICKOETA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LZNWYQJJBLGYLT-UHFFFAOYSA-N tenoxicam Chemical compound OC=1C=2SC=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LZNWYQJJBLGYLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 50
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- YXNDIUKTRLHPOM-UHFFFAOYSA-N 3-sulfothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1S(O)(=O)=O YXNDIUKTRLHPOM-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- PJVJBDAUWILEOG-UHFFFAOYSA-N methyl 3-chlorosulfonylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1S(Cl)(=O)=O PJVJBDAUWILEOG-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- BXEAAHIHFFIMIE-UHFFFAOYSA-N 3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Cl BXEAAHIHFFIMIE-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- OKNMAOBDSCJUDO-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxothieno[2,3-e]thiazine-3-carboxylate Chemical compound O=S1(=O)N(C)C(C(=O)OC)=C(O)C2=C1C=CS2 OKNMAOBDSCJUDO-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RVOCCTALZIEBJL-UHFFFAOYSA-N 3-chlorosulfonylthiophene-2-carbonyl chloride Chemical compound ClC(=O)C=1SC=CC=1S(Cl)(=O)=O RVOCCTALZIEBJL-UHFFFAOYSA-N 0.000 description 4
- QPYFNTQGFUWDDP-UHFFFAOYSA-N 4-chlorothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1Cl QPYFNTQGFUWDDP-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 208000000114 Pain Threshold Diseases 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000037040 pain threshold Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GTRUHHWLEREHBP-UHFFFAOYSA-N methyl 3-(methylsulfamoyl)thiophene-2-carboxylate Chemical compound CNS(=O)(=O)C=1C=CSC=1C(=O)OC GTRUHHWLEREHBP-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 230000001562 ulcerogenic effect Effects 0.000 description 3
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 2
- LSDJRBFOXKCGFY-UHFFFAOYSA-N 2-chloro-n-(1,3-thiazol-2-yl)acetamide Chemical compound ClCC(=O)NC1=NC=CS1 LSDJRBFOXKCGFY-UHFFFAOYSA-N 0.000 description 2
- AYKJLZKNHNYZON-UHFFFAOYSA-N 2-methoxycarbonylthiophene-3-sulfonic acid Chemical compound COC(=O)C=1SC=CC=1S(O)(=O)=O AYKJLZKNHNYZON-UHFFFAOYSA-N 0.000 description 2
- APBIZVFQQBCAAT-UHFFFAOYSA-N 4-bromothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1Br APBIZVFQQBCAAT-UHFFFAOYSA-N 0.000 description 2
- LIFXVYYBEWUQDC-UHFFFAOYSA-N 4-chlorosulfonylthiophene-3-carbonyl chloride Chemical compound ClC(=O)C1=CSC=C1S(Cl)(=O)=O LIFXVYYBEWUQDC-UHFFFAOYSA-N 0.000 description 2
- XINKHPPAHJZEQZ-UHFFFAOYSA-N 4-chlorothiophene-3-carbonyl chloride Chemical compound ClC(=O)C1=CSC=C1Cl XINKHPPAHJZEQZ-UHFFFAOYSA-N 0.000 description 2
- ACBUQOCRIKFKLJ-UHFFFAOYSA-N 4-methoxycarbonylthiophene-3-sulfonic acid Chemical compound COC(=O)C1=CSC=C1S(O)(=O)=O ACBUQOCRIKFKLJ-UHFFFAOYSA-N 0.000 description 2
- BSLGMUKWYRKFDT-UHFFFAOYSA-N 4-sulfothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1S(O)(=O)=O BSLGMUKWYRKFDT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000025865 Ulcer Diseases 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
- 239000003929 acidic solution Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- UPOAVKOVNHTJLW-UHFFFAOYSA-N ethyl 2-(4-hydroxy-1,1-dioxo-2h-thieno[2,3-e]thiazin-3-yl)acetate Chemical compound O=S1(=O)NC(CC(=O)OCC)=C(O)C2=C1C=CS2 UPOAVKOVNHTJLW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000001156 gastric mucosa Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- SEMVRXMFCHXUMD-UHFFFAOYSA-N methyl 3-hydroxythiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1O SEMVRXMFCHXUMD-UHFFFAOYSA-N 0.000 description 2
- YXEPIWFYDPPQTC-UHFFFAOYSA-N methyl 4-(methylsulfamoyl)thiophene-3-carboxylate Chemical compound CNS(=O)(=O)C1=CSC=C1C(=O)OC YXEPIWFYDPPQTC-UHFFFAOYSA-N 0.000 description 2
- MRFIBCNQYJJOPN-UHFFFAOYSA-N methyl 4-chlorosulfonylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(Cl)(=O)=O MRFIBCNQYJJOPN-UHFFFAOYSA-N 0.000 description 2
- LKQAXYCQTJUNIX-UHFFFAOYSA-N methyl 4-hydroxy-2-methyl-1,1-dioxothieno[3,4-e]thiazine-3-carboxylate Chemical compound O=S1(=O)N(C)C(C(=O)OC)=C(O)C2=CSC=C21 LKQAXYCQTJUNIX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- GZLPFEYTAAXJCP-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-sulfonyl chloride Chemical group CC1=NOC(C)=C1S(Cl)(=O)=O GZLPFEYTAAXJCP-UHFFFAOYSA-N 0.000 description 1
- GCPHKTQMABHWPY-UHFFFAOYSA-N 3-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C=1SC=CC=1Cl GCPHKTQMABHWPY-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- NRAVSUNXRBRPRE-UHFFFAOYSA-N 3-sulfamoylthiophene-2-carboxylic acid Chemical compound NS(=O)(=O)C=1C=CSC=1C(O)=O NRAVSUNXRBRPRE-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000007281 aminoalkylation reaction Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 239000000872 buffer Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- JFJBXZHAHLUMHH-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-methyl-1,1-dioxothieno[2,3-e]thiazin-3-yl)acetate Chemical compound O=S1(=O)N(C)C(CC(=O)OCC)=C(O)C2=C1C=CS2 JFJBXZHAHLUMHH-UHFFFAOYSA-N 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- NIDZUMSLERGAON-UHFFFAOYSA-N ethyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CCOC(=O)CNC NIDZUMSLERGAON-UHFFFAOYSA-N 0.000 description 1
- DSFQXPBZWOOJOW-UHFFFAOYSA-N ethyl 4-hydroxy-1,1-dioxo-2h-thieno[2,3-e]thiazine-3-carboxylate Chemical compound O=S1(=O)NC(C(=O)OCC)=C(O)C2=C1C=CS2 DSFQXPBZWOOJOW-UHFFFAOYSA-N 0.000 description 1
- MFFXVVHUKRKXCI-UHFFFAOYSA-N ethyl iodoacetate Chemical compound CCOC(=O)CI MFFXVVHUKRKXCI-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 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
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- CNQASVUJPHFCTE-UHFFFAOYSA-N methyl 4-[(2-methoxy-2-oxoethyl)-methylsulfamoyl]thiophene-3-carboxylate Chemical compound COC(=O)CN(C)S(=O)(=O)C1=CSC=C1C(=O)OC CNQASVUJPHFCTE-UHFFFAOYSA-N 0.000 description 1
- LPALJGZYPGQIER-UHFFFAOYSA-N methyl 4-oxothiophene-3-carboxylate Chemical compound COC(=O)C1=CSCC1=O LPALJGZYPGQIER-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940099259 vaseline Drugs 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
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Electroplating Methods And Accessories (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1158274A CH608500A5 (en) | 1974-08-26 | 1974-08-26 | Process for the preparation of thiazine derivatives |
| CH1215774A CH608501A5 (en) | 1974-09-09 | 1974-09-09 | Process for the preparation of thiazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2537070A1 DE2537070A1 (de) | 1976-03-18 |
| DE2537070C2 true DE2537070C2 (hu) | 1987-06-25 |
Family
ID=25708582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752537070 Granted DE2537070A1 (de) | 1974-08-26 | 1975-08-20 | Thiazinderivate |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5826758B2 (hu) |
| AR (1) | AR216288A1 (hu) |
| AT (1) | AT350064B (hu) |
| BR (1) | BR7505463A (hu) |
| DD (1) | DD124119A5 (hu) |
| DE (1) | DE2537070A1 (hu) |
| DK (1) | DK137835B (hu) |
| FI (1) | FI59253C (hu) |
| FR (3) | FR2282893A1 (hu) |
| GB (1) | GB1519811A (hu) |
| HU (1) | HU173739B (hu) |
| IE (1) | IE41457B1 (hu) |
| IL (1) | IL47877A (hu) |
| LU (2) | LU73257A1 (hu) |
| NL (2) | NL183582C (hu) |
| NO (1) | NO146096C (hu) |
| PL (1) | PL106076B1 (hu) |
| SE (1) | SE412066B (hu) |
| SU (1) | SU603338A3 (hu) |
| YU (1) | YU40266B (hu) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704485A1 (de) * | 1977-02-03 | 1978-08-10 | Thomae Gmbh Dr K | Neue 2,5-dihydro-1,2-thiazino eckige klammer auf 5,6-b eckige klammer zu indol-3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| LU78009A1 (de) * | 1977-08-22 | 1979-05-23 | Hoffmann La Roche | Verfahren zur herstellung von thiazinderivaten |
| ZA784958B (en) * | 1977-09-06 | 1979-08-29 | Hoffmann La Roche | Thiazine derivatives |
| AU518216B2 (en) * | 1977-09-06 | 1981-09-17 | Hafslund Nycomed Pharma Aktiengesellschaft | Thienothiazine derivatives |
| DE2838377A1 (de) * | 1978-09-02 | 1980-03-20 | Thomae Gmbh Dr K | Neue 4-hydroxy-2h eckige klammer auf 1 eckige klammer zu benzothieno eckige klammer auf 2,3-e eckige klammer zu -1,2- thiazin-3-carboxamid-1,1-dioxide sowie deren salze, deren verwendung und verfahren zu ihrer herstellung |
| AU5811280A (en) * | 1979-06-13 | 1980-12-18 | F. Hoffmann-La Roche Ag | Thiazine derivatives |
| JPS58109492A (ja) * | 1981-12-22 | 1983-06-29 | Mitsui Toatsu Chem Inc | チエノチアジン誘導体およびそれを含有する医薬組成物 |
| ATE26720T1 (de) * | 1982-09-09 | 1987-05-15 | Hoffmann La Roche | Thieno(2,3-e)-1,2-thiazin-derivate. |
| JPS60163533U (ja) * | 1984-04-02 | 1985-10-30 | ホシデン株式会社 | リ−ル台の制動装置 |
| JPH0318748Y2 (hu) * | 1985-12-18 | 1991-04-19 | ||
| ATA39088A (de) | 1988-02-18 | 1990-06-15 | Binder Dieter Dr | Basisch substituierte thienoisothiazol-3(2h)-on-1,1-dioxide und ihre pharmazeutisch vertraeglichen salze, verfahren zu ihrer herstellung und ihre verwendung |
| AT400568B (de) * | 1994-05-18 | 1996-01-25 | Chem Pharm Forsch Gmbh | Neue n-heterocyclische thienothiazincarboxamide, verfahren zu ihrer herstellung und ihre verwendung |
| AT400437B (de) * | 1993-12-14 | 1995-12-27 | Chem Pharm Forsch Gmbh | Neue n-heterocyclische thienothiazincarboxamide, verfahren zu ihrer herstellung und ihre verwendung |
| EP0658559A1 (de) * | 1993-12-14 | 1995-06-21 | Chemisch Pharmazeutische Forschungsgesellschaft m.b.H. | Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als 5-dipoxygenase und Cyclooxygenaseinhibitoren |
| US5538966A (en) * | 1994-01-21 | 1996-07-23 | Alcon Laboratories, Inc. | Carbonic anhydrase inhibitors |
| IT1308633B1 (it) | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
| CN1171892C (zh) * | 2001-06-25 | 2004-10-20 | 李晶 | 具有抗炎镇痛活性的噻吩并噻嗪化合物及其制备方法和用途 |
-
1975
- 1975-08-05 IL IL47877A patent/IL47877A/xx unknown
- 1975-08-20 DE DE19752537070 patent/DE2537070A1/de active Granted
- 1975-08-22 FR FR7525999A patent/FR2282893A1/fr active Granted
- 1975-08-22 AR AR260104A patent/AR216288A1/es active
- 1975-08-22 GB GB34943/75A patent/GB1519811A/en not_active Expired
- 1975-08-25 AT AT655975A patent/AT350064B/de active Protection Beyond IP Right Term
- 1975-08-25 SU SU752167373A patent/SU603338A3/ru active
- 1975-08-25 SE SE7509446A patent/SE412066B/xx not_active IP Right Cessation
- 1975-08-25 DK DK381175AA patent/DK137835B/da not_active IP Right Cessation
- 1975-08-25 DD DD188010A patent/DD124119A5/xx unknown
- 1975-08-25 HU HU75HO1829A patent/HU173739B/hu unknown
- 1975-08-25 IE IE1856/75A patent/IE41457B1/en not_active IP Right Cessation
- 1975-08-26 JP JP50102635A patent/JPS5826758B2/ja not_active Expired
- 1975-08-26 YU YU2166/75A patent/YU40266B/xx unknown
- 1975-08-26 NO NO752932A patent/NO146096C/no unknown
- 1975-08-26 NL NLAANVRAGE7510057,A patent/NL183582C/xx active Protection Beyond IP Right Term
- 1975-08-26 FI FI752398A patent/FI59253C/fi not_active IP Right Cessation
- 1975-08-26 LU LU73257A patent/LU73257A1/xx active Protection Beyond IP Right Term
- 1975-08-26 PL PL1975182921A patent/PL106076B1/pl unknown
- 1975-08-26 BR BR7505463*A patent/BR7505463A/pt unknown
-
1976
- 1976-05-21 FR FR7615424A patent/FR2303803A1/fr active Granted
- 1976-05-21 FR FR7615425A patent/FR2309558A1/fr active Granted
-
1993
- 1993-06-16 LU LU88312C patent/LU88312I2/de unknown
- 1993-06-17 NL NL930080C patent/NL930080I2/nl unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: F. HOFFMANN-LA ROCHE AG, BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: LEDERER, F., DIPL.-CHEM. DR., 8000 MUENCHEN RIEDERER FRHR. VON PAAR ZU SCHOENAU, A., DIPL.-ING., PAT.-ANWAELTE, 8300 LANDSHUT |