CH496726A - Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3,4-thiadiazin-5-onen - Google Patents
Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3,4-thiadiazin-5-onenInfo
- Publication number
- CH496726A CH496726A CH735268A CH735268A CH496726A CH 496726 A CH496726 A CH 496726A CH 735268 A CH735268 A CH 735268A CH 735268 A CH735268 A CH 735268A CH 496726 A CH496726 A CH 496726A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- thiadiazol
- methyl
- dihydro
- ium
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- -1 1, 3,4-thiadiazolium compound Chemical class 0.000 claims description 134
- 238000000034 method Methods 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- AWVDQIMIPOMCGC-UHFFFAOYSA-N 4h-1,3,4-thiadiazin-5-one Chemical class O=C1CSC=NN1 AWVDQIMIPOMCGC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- HYVIKAGUFABXQB-UHFFFAOYSA-N benzoyloxyphosphinic acid Chemical compound OP(=O)OC(=O)C1=CC=CC=C1 HYVIKAGUFABXQB-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical group 0.000 claims 1
- YEMKIGUKNDOZEG-UHFFFAOYSA-N phosphonoacetaldehyde Chemical compound OP(O)(=O)CC=O YEMKIGUKNDOZEG-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 14
- TZAMQIAPGYOUKF-UHFFFAOYSA-N diethoxyphosphoryl(phenyl)methanone Chemical compound CCOP(=O)(OCC)C(=O)C1=CC=CC=C1 TZAMQIAPGYOUKF-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
- 230000003501 anti-edematous effect Effects 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CWBBOZLURZLOPO-UHFFFAOYSA-M 2-methyl-5-[(5-phenyl-1,3,4-thiadiazol-3-ium-3-yl)methyl]pyrimidin-4-amine bromide hydrobromide Chemical compound Br.[Br-].CC1=NC=C(C(=N1)N)C[N+]1=CSC(=N1)C1=CC=CC=C1 CWBBOZLURZLOPO-UHFFFAOYSA-M 0.000 description 3
- CNFHSSLQUQKFEU-UHFFFAOYSA-M 3-benzyl-5-phenyl-1,3,4-thiadiazol-3-ium bromide Chemical compound [Br-].C(C1=CC=CC=C1)[N+]1=CSC(=N1)C1=CC=CC=C1 CNFHSSLQUQKFEU-UHFFFAOYSA-M 0.000 description 3
- AHDWHXWPSSJKBB-UHFFFAOYSA-M 3-methyl-5-phenyl-1,3,4-thiadiazol-3-ium iodide Chemical compound [I-].C[N+]1=CSC(=N1)C1=CC=CC=C1 AHDWHXWPSSJKBB-UHFFFAOYSA-M 0.000 description 3
- UKCCMRKWPQOFCW-UHFFFAOYSA-N 4-[(4-amino-2-methylpyrimidin-5-yl)methyl]-6-phenyl-1,3,4-thiadiazin-5-one Chemical compound NC1=NC(C)=NC=C1CN1C(=O)C(C=2C=CC=CC=2)SC=N1 UKCCMRKWPQOFCW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000008338 1,3,4-thiadiazines Chemical class 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- MBICAYCUFJITIX-UHFFFAOYSA-M 3-benzyl-1,3,4-thiadiazol-3-ium;chloride Chemical compound [Cl-].C=1SC=N[N+]=1CC1=CC=CC=C1 MBICAYCUFJITIX-UHFFFAOYSA-M 0.000 description 2
- FWFSMPPFTZGMQH-UHFFFAOYSA-N 4-benzyl-6-methyl-2-phenyl-1,3,4-thiadiazin-5-one Chemical compound C1(=CC=CC=C1)C=1SC(C(N(N1)CC1=CC=CC=C1)=O)C FWFSMPPFTZGMQH-UHFFFAOYSA-N 0.000 description 2
- ILIMOXLCMLLSSU-UHFFFAOYSA-N 4-benzyl-6-phenyl-1,3,4-thiadiazin-5-one Chemical compound C(C1=CC=CC=C1)N1N=CSC(C1=O)C1=CC=CC=C1 ILIMOXLCMLLSSU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RBBGLMFXNAWUJD-UHFFFAOYSA-M Br.[Br-].CC1=NC=C(C(=N1)N)C[N+]1=CSC=N1 Chemical compound Br.[Br-].CC1=NC=C(C(=N1)N)C[N+]1=CSC=N1 RBBGLMFXNAWUJD-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NVRJBVYGMNCXFC-UHFFFAOYSA-N 1-[methoxy(phenyl)phosphoryl]-2-phenylethanone Chemical compound C=1C=CC=CC=1P(=O)(OC)C(=O)CC1=CC=CC=C1 NVRJBVYGMNCXFC-UHFFFAOYSA-N 0.000 description 1
- YOHJPFQGGNEGSE-UHFFFAOYSA-N 1-diethoxyphosphorylethanone Chemical compound CCOP(=O)(C(C)=O)OCC YOHJPFQGGNEGSE-UHFFFAOYSA-N 0.000 description 1
- NOEKTFIMLDEDMC-UHFFFAOYSA-N 1-dimethoxyphosphoryl-2-phenylethanone Chemical compound COP(=O)(OC)C(=O)CC1=CC=CC=C1 NOEKTFIMLDEDMC-UHFFFAOYSA-N 0.000 description 1
- RCBRPJRYJDTVCW-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenylpropan-1-one Chemical compound COP(=O)(OC)C(=O)CCC1=CC=CC=C1 RCBRPJRYJDTVCW-UHFFFAOYSA-N 0.000 description 1
- TXXSHMJSGVBRDC-UHFFFAOYSA-N 2-methylpropanoylphosphonic acid Chemical compound CC(C)C(=O)P(O)(O)=O TXXSHMJSGVBRDC-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MUWRJXDPLRGBIZ-UHFFFAOYSA-M 3-benzyl-1,3,4-thiadiazol-3-ium;iodide Chemical compound [I-].C=1SC=N[N+]=1CC1=CC=CC=C1 MUWRJXDPLRGBIZ-UHFFFAOYSA-M 0.000 description 1
- DIZIEUCFEVBBPS-UHFFFAOYSA-M 3-methyl-5-phenyl-1,3,4-thiadiazol-3-ium;chloride Chemical compound [Cl-].C[N+]1=CSC(C=2C=CC=CC=2)=N1 DIZIEUCFEVBBPS-UHFFFAOYSA-M 0.000 description 1
- NNMNNKUDTCUEED-UHFFFAOYSA-N 3-methylbut-2-enoylphosphonic acid Chemical compound CC(C)=CC(=O)P(O)(O)=O NNMNNKUDTCUEED-UHFFFAOYSA-N 0.000 description 1
- CBSXYJDLOWATMK-UHFFFAOYSA-N 4-methyl-2,6-diphenyl-1,3,4-thiadiazin-5-one Chemical compound O=C1N(C)N=C(C=2C=CC=CC=2)SC1C1=CC=CC=C1 CBSXYJDLOWATMK-UHFFFAOYSA-N 0.000 description 1
- BKQZHNHRKIQZGY-UHFFFAOYSA-N C1(=CC=CC=C1)C=1SC(C(N(N1)CC=1C(=NC(=NC1)C)N)=O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C=1SC(C(N(N1)CC=1C(=NC(=NC1)C)N)=O)C1=CC=CC=C1 BKQZHNHRKIQZGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- MPTWHSMGXLTEFV-UHFFFAOYSA-N [ethoxy(phenyl)phosphoryl]-phenylmethanone Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=CC=CC=C1 MPTWHSMGXLTEFV-UHFFFAOYSA-N 0.000 description 1
- GKMKJRYNJIFULH-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]-phenylmethanone Chemical compound C=1C=CC=CC=1P(=O)(OC)C(=O)C1=CC=CC=C1 GKMKJRYNJIFULH-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3129967 | 1967-05-17 | ||
| JP6186367 | 1967-09-26 | ||
| JP6186467 | 1967-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496726A true CH496726A (de) | 1970-09-30 |
Family
ID=27287278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH735268A CH496726A (de) | 1967-05-17 | 1968-05-17 | Verfahren zur Herstellung von 5,6-Dihydro-4H-1,3,4-thiadiazin-5-onen |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3514455A (en, 2012) |
| CH (1) | CH496726A (en, 2012) |
| FR (1) | FR8169M (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4104381A (en) * | 1973-05-03 | 1978-08-01 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
| US4158732A (en) * | 1978-03-24 | 1979-06-19 | Chevron Research Company | Process for production of 2-substituted-imino-3-alkyl-tetrahydro-6H-1,3,4-thiadiazin-5-ones |
| US4144335A (en) * | 1978-03-24 | 1979-03-13 | Chevron Research Company | Insecticidal 2-substituted-imino-3-alkyl-5-dialkoxyphosphinothioyloxy-6H-1,3,4-thiadiazine |
| EP0052442B1 (en) * | 1980-11-14 | 1985-09-11 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
-
1968
- 1968-05-16 FR FR152059A patent/FR8169M/fr not_active Expired
- 1968-05-17 CH CH735268A patent/CH496726A/de not_active IP Right Cessation
- 1968-05-17 US US729898A patent/US3514455A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770449B2 (de) | 1975-08-07 |
| DE1770449A1 (de) | 1972-01-27 |
| FR8169M (en, 2012) | 1970-08-31 |
| US3514455A (en) | 1970-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |