CH624960A5 - Process for the preparation of thiazine derivatives - Google Patents

Process for the preparation of thiazine derivatives Download PDF

Info

Publication number: CH624960A5
Authority: CH; Switzerland
Prior art keywords: methyl; pyridyl; lower alkyl; formula; thiazolyl
Prior art date: 1976-02-23

Application number

CH8377A

Other languages

German (de)

English (en)

Inventor

Dieter Prof Dr Binder

Otto Prof Dr Hromatka

Rudolf Dr Pfister

Paul Dr Zeller

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-02-23

Filing date

1977-01-05

Publication date

1981-08-31

1977-01-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1977-02-07 Priority to MC771230A priority Critical patent/MC1135A1/fr

1977-02-09 Priority to US05/767,016 priority patent/US4090020A/en

1977-02-10 Priority to NL7701419A priority patent/NL7701419A/xx

1977-02-16 Priority to IL51467A priority patent/IL51467A0/xx

1977-02-16 Priority to AU22349/77A priority patent/AU2234977A/en

1977-02-17 Priority to DE19772706859 priority patent/DE2706859A1/de

1977-02-18 Priority to AR266597A priority patent/AR214626A1/es

1977-02-18 Priority to LU76801A priority patent/LU76801A1/xx

1977-02-18 Priority to NZ183374A priority patent/NZ183374A/xx

1977-02-18 Priority to PT66207A priority patent/PT66207B/pt

1977-02-21 Priority to JP52017270A priority patent/JPS6019317B2/ja

1977-02-21 Priority to FR7704897A priority patent/FR2341584A1/fr

1977-02-22 Priority to GB7377/77A priority patent/GB1561521A/en

1977-02-22 Priority to ES456400A priority patent/ES456400A1/es

1977-02-22 Priority to HU77HO1960A priority patent/HU173075B/hu

1977-02-22 Priority to GR52813A priority patent/GR63177B/el

1978-03-02 Priority to US05/882,723 priority patent/US4175085A/en

1981-08-31 Publication of CH624960A5 publication Critical patent/CH624960A5/de

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 7
150000004897 thiazines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 35
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 15
125000005842 heteroatom Chemical group 0.000 claims abstract description 7
TZIJDLHRFZUDHD-UHFFFAOYSA-N 2h-thieno[2,3-e]thiazine Chemical class C1=CNSC2=C1SC=C2 TZIJDLHRFZUDHD-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 3
-1 2-thiazolyl Chemical group 0.000 claims description 78
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
SFXSIUXCLWRDSG-UHFFFAOYSA-N 2-methyl-3-oxo-n-pyridin-2-yl-4h-thieno[2,3-e]thiazine-4-carboxamide Chemical compound O=C1N(C)SC=2C=CSC=2C1C(=O)NC1=CC=CC=N1 SFXSIUXCLWRDSG-UHFFFAOYSA-N 0.000 claims description 2
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
PNCOVLNYANEBLP-UHFFFAOYSA-N 3-hydroxy-2-methyl-1,1-dioxo-N-pyrazin-2-ylthieno[2,3-e]thiazine-4-carboxamide Chemical compound C1=2SC=CC=2S(=O)(=O)N(C)C(O)=C1C(=O)NC1=CN=CC=N1 PNCOVLNYANEBLP-UHFFFAOYSA-N 0.000 claims description 2
UCZNOTZQRQIHMW-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-oxo-N-(1,3-thiazol-2-yl)thiolane-3-carboxamide Chemical compound CC1(SCC(C1=O)C(NC=1SC=CN1)=O)O UCZNOTZQRQIHMW-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
230000003356 anti-rheumatic effect Effects 0.000 abstract description 2
230000002785 anti-thrombosis Effects 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
239000003435 antirheumatic agent Substances 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 11
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000001816 cooling Methods 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000010438 heat treatment Methods 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
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
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 4
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
208000000114 Pain Threshold Diseases 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
UHIHALQFJZYXPX-UHFFFAOYSA-N methyl 2-methyl-1,1,3-trioxo-4h-thieno[2,3-e]thiazine-4-carboxylate Chemical compound O=S1(=O)N(C)C(=O)C(C(=O)OC)C2=C1C=CS2 UHIHALQFJZYXPX-UHFFFAOYSA-N 0.000 description 3
230000037040 pain threshold Effects 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-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
NVUNRWVGRDVKGV-UHFFFAOYSA-N 3-(methylsulfamoyl)thiophene-2-carboxylic acid Chemical compound CNS(=O)(=O)C=1C=CSC=1C(O)=O NVUNRWVGRDVKGV-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000012320 chlorinating reagent Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
230000004054 inflammatory process Effects 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
LWVYQLFZYBMBIS-UHFFFAOYSA-N methyl 2-[3-(methylsulfamoyl)thiophen-2-yl]acetate Chemical compound CNS(=O)(=O)C=1C=CSC=1CC(=O)OC LWVYQLFZYBMBIS-UHFFFAOYSA-N 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
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OLKCFBIDOLYFMW-UHFFFAOYSA-N 2-[3-(methylsulfamoyl)thiophen-2-yl]acetic acid Chemical compound CNS(=O)(=O)C=1C=CSC=1CC(O)=O OLKCFBIDOLYFMW-UHFFFAOYSA-N 0.000 description 1
NMRGHOBCFLHAQQ-UHFFFAOYSA-N 2-diazonio-1-[3-(methylsulfamoyl)thiophen-2-yl]ethenolate Chemical compound CNS(=O)(=O)C=1C=CSC=1C(=O)C=[N+]=[N-] NMRGHOBCFLHAQQ-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
UBLAPDKZBWKHDM-UHFFFAOYSA-N 2-methyl-1,1,3-trioxo-n-(1,3-thiazol-2-yl)-4h-thieno[2,3-e]thiazine-4-carboxamide Chemical compound C1=2SC=CC=2S(=O)(=O)N(C)C(=O)C1C(=O)NC1=NC=CS1 UBLAPDKZBWKHDM-UHFFFAOYSA-N 0.000 description 1
JLNQAEJWHMSZRH-UHFFFAOYSA-N 2-methyl-1,1,3-trioxo-n-pyridin-2-yl-4h-thieno[2,3-e]thiazine-4-carboxamide Chemical compound C1=2SC=CC=2S(=O)(=O)N(C)C(=O)C1C(=O)NC1=CC=CC=N1 JLNQAEJWHMSZRH-UHFFFAOYSA-N 0.000 description 1
MLVRYXCWVRQSLN-UHFFFAOYSA-N 2-methyl-1,1-dioxo-4h-thieno[2,3-e]thiazin-3-one Chemical compound O=S1(=O)N(C)C(=O)CC2=C1C=CS2 MLVRYXCWVRQSLN-UHFFFAOYSA-N 0.000 description 1
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 1
GCPHKTQMABHWPY-UHFFFAOYSA-N 3-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C=1SC=CC=1Cl GCPHKTQMABHWPY-UHFFFAOYSA-N 0.000 description 1
ZYJSTSMEUKNCEV-UHFFFAOYSA-N 3-diazo-1-diazonioprop-1-en-2-olate Chemical compound [N-]=[N+]=CC(=O)C=[N+]=[N-] ZYJSTSMEUKNCEV-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 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
230000003502 anti-nociceptive effect Effects 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 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
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000706 filtrate 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
239000011521 glass Substances 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
125000000623 heterocyclic group Chemical group 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
MFMHSHUBCUWWSK-UHFFFAOYSA-N methyl 2-[3-[methoxycarbonyl(methyl)sulfamoyl]thiophen-2-yl]acetate Chemical compound COC(=O)CC=1SC=CC=1S(=O)(=O)N(C)C(=O)OC MFMHSHUBCUWWSK-UHFFFAOYSA-N 0.000 description 1
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 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 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
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 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
125000001424 substituent group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH8377A 1976-02-23 1977-01-05 Process for the preparation of thiazine derivatives CH624960A5 (en)

Priority Applications (17)

Application Number	Priority Date	Filing Date	Title
MC771230A MC1135A1 (fr)	1976-02-23	1977-02-07	Derives de thiazine
US05/767,016 US4090020A (en)	1976-02-23	1977-02-09	Thienothiazine derivatives
NL7701419A NL7701419A (nl)	1976-02-23	1977-02-10	Thiazinederivaten.
IL51467A IL51467A0 (en)	1976-02-23	1977-02-16	Novel thiazine derivatives their preparation and pharmaceutical compositions containing them
AU22349/77A AU2234977A (en)	1976-02-23	1977-02-16	Thiazine derivatives
DE19772706859 DE2706859A1 (de)	1976-02-23	1977-02-17	Thiazinderivate
AR266597A AR214626A1 (es)	1976-02-23	1977-02-18	Procedimiento para preparar derivados de 1,1-dioxido de 4-carbamoil sustituida 3,4-dihidro-3-oxo-2h-tieno(2,3-e)-1,2-tiazina
LU76801A LU76801A1 (fr)	1976-02-23	1977-02-18
NZ183374A NZ183374A (en)	1976-02-23	1977-02-18	3-oxo-4-substituted carbamoyl-2-alkyl-3,4-dihydro-2h-thieno-(2,3,-e)(1,2)thiazine 1,1-dioxides
PT66207A PT66207B (en)	1976-02-23	1977-02-18	Process for the preparation of thiazine derivatives
JP52017270A JPS6019317B2 (ja)	1976-02-23	1977-02-21	チエノチアジン誘導体及びその製造方法
FR7704897A FR2341584A1 (fr)	1976-02-23	1977-02-21	Nouveaux derives de thienothiazine, leur procede de preparation et leur application en tant que medicaments
GB7377/77A GB1561521A (en)	1976-02-23	1977-02-22	3,4 - dihydro - 3 - oxo - 4-carbamoyl - 2h - thieno (2,3 - e) - 1 - 2-thiazine 1,1 - dioxide derivatives
ES456400A ES456400A1 (es)	1976-02-23	1977-02-22	Un procedimiento para la preparacion de derivados de tieno- tiacina.
HU77HO1960A HU173075B (hu)	1976-02-23	1977-02-22	Sposob poluchenija proizvodnykh tieno-skobka-2,3-e-skobkka zakryta-tiazina
GR52813A GR63177B (en)	1976-02-23	1977-02-22	Preparation process of thiazine derivatives
US05/882,723 US4175085A (en)	1976-02-23	1978-03-02	Thienothiazine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT126876A AT347962B (de)	1976-02-23	1976-02-23	Verfahren zur herstellung von neuen thienothiazinderivaten

Publications (1)

Publication Number	Publication Date
CH624960A5 true CH624960A5 (en)	1981-08-31

Family

ID=3510204

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH8377A CH624960A5 (en)	1976-02-23	1977-01-05	Process for the preparation of thiazine derivatives
CH129981A CH626372A5 (en)	1976-02-23	1981-02-26	Process for the preparation of thiazine derivatives

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH129981A CH626372A5 (en)	1976-02-23	1981-02-26	Process for the preparation of thiazine derivatives

Country Status (4)

Country	Link
AT (1)	AT347962B (fr)
BE (1)	BE851686A (fr)
CH (2)	CH624960A5 (fr)
ZA (1)	ZA77935B (fr)

1976
- 1976-02-23 AT AT126876A patent/AT347962B/de not_active IP Right Cessation
1977
- 1977-01-05 CH CH8377A patent/CH624960A5/de not_active IP Right Cessation
- 1977-02-16 ZA ZA770935A patent/ZA77935B/xx unknown
- 1977-02-22 BE BE175135A patent/BE851686A/fr unknown
1981
- 1981-02-26 CH CH129981A patent/CH626372A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE851686A (fr)	1977-08-22
ZA77935B (en)	1977-12-28
CH626372A5 (en)	1981-11-13
ATA126876A (de)	1978-06-15
AT347962B (de)	1979-01-25

Legal Events

Date	Code	Title	Description
1987-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001113B1 (fr)	1981-11-11	Dérivés de thiénothiazine, leur préparation et compositions les contenant
DE2537070C2 (fr)	1987-06-25
DE2655009A1 (de)	1978-06-15	Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
DE3850308T2 (de)	1994-10-06	Tetrahydroisochinolin-2-yl-Derivate als Thromboxan A2-Antagonisten.
DE68924221T2 (de)	1996-02-15	Imidazolderivate.
DE2435382A1 (de)	1975-02-13	Pyrimidobenzothiadiazepine und pyrimidothiadiazocine und ihre dioxide, verfahren zu ihrer herstellung und arzneimittel
DE3781703T2 (de)	1993-02-18	2-benzimidazolylalkylthio(oder sulfinyl- oder sulfonyl)-derivate, verfahren zu deren herstellung und deren anwendung als arzneimittel.
DE69303605T2 (de)	1997-01-23	Unverbrückte bis-aryl-carbinol-derivate, zusammensetzungen und ihre verwendung
DE2706859A1 (de)	1977-08-25	Thiazinderivate
DE3804346A1 (de)	1989-08-24	Tert.-butylphenyl-pyridyl-amide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
DE3017977A1 (de)	1981-11-19	Neue substituierte 2(3h)-benzothiazolone
CH640540A5 (de)	1984-01-13	Thieno-thiazinderivate.
CH619236A5 (en)	1980-09-15	Process for the preparation of thienothiazine derivatives
CH624960A5 (en)	1981-08-31	Process for the preparation of thiazine derivatives
EP0427161B1 (fr)	1994-04-20	Picolylsélénobenzamides d'aminopyridines, d'anilines et de picolylamines
CH617705A5 (en)	1980-06-13	Process for the preparation of thienothiazine derivatives
DE2854112A1 (de)	1979-07-12	Neue pyrido-pyrimidine, verfahren zu ihrer herstellung und diese verbindungen enthaltenden arzneimittel
DE2521326A1 (de)	1975-11-27	Neue thienodiazepinderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel
EP0021058A2 (fr)	1981-01-07	Dérivés de la benzothiénothiazine, leur application, procédé et intermédiaires pour leur préparation et médicaments les contenant
DD236929A5 (de)	1986-06-25	Verfahren zur herstellung von benzazolderivaten
AT365199B (de)	1981-12-28	Verfahren zur herstellung von neuen thienothiazin-derivaten und von deren salzen
DE1770177A1 (de)	1972-03-16	Monoaryl-substituierte Oxazole
DE2107301A1 (de)	1971-09-09	Neue heterocyclische Verbindungen und Verfahren zu ihrer Herstellung
AT352745B (de)	1979-10-10	Verfahren zur herstellung von neuen thienothiazinderivaten
CH608500A5 (en)	1979-01-15	Process for the preparation of thiazine derivatives