JPS5913516B2 - 新規２−アミノ−１，３−チアジン類の製造方法 - Google Patents
新規２−アミノ−１，３−チアジン類の製造方法Info
- Publication number
- JPS5913516B2 JPS5913516B2 JP50063556A JP6355675A JPS5913516B2 JP S5913516 B2 JPS5913516 B2 JP S5913516B2 JP 50063556 A JP50063556 A JP 50063556A JP 6355675 A JP6355675 A JP 6355675A JP S5913516 B2 JPS5913516 B2 JP S5913516B2
- Authority
- JP
- Japan
- Prior art keywords
- thiazine
- amino
- weight
- formula
- ketone
- 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
- QKFOHTNLZOIEHZ-UHFFFAOYSA-N 2h-1,3-thiazin-2-amine Chemical class NC1SC=CC=N1 QKFOHTNLZOIEHZ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- -1 isobutenyl Chemical group 0.000 description 11
- 235000015097 nutrients Nutrition 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 244000005700 microbiome Species 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical compound C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 241000195493 Cryptophyta Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 241000589652 Xanthomonas oryzae Species 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000186216 Corynebacterium Species 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 241001467460 Myxogastria Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000003621 irrigation water Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VAPHYEWCMFDPRS-UHFFFAOYSA-N 3,4-dihydro-2h-1,3-thiazin-2-ol Chemical compound OC1NCC=CS1 VAPHYEWCMFDPRS-UHFFFAOYSA-N 0.000 description 2
- KTJRGPZVSKWRTJ-UHFFFAOYSA-N 3-chloro-1-phenylpropan-1-one Chemical compound ClCCC(=O)C1=CC=CC=C1 KTJRGPZVSKWRTJ-UHFFFAOYSA-N 0.000 description 2
- HEVOEMIYAOINPM-UHFFFAOYSA-N 4-phenyl-2h-1,3-thiazin-2-amine;hydrochloride Chemical compound Cl.NC1SC=CC(C=2C=CC=CC=2)=N1 HEVOEMIYAOINPM-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588698 Erwinia Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 241001123663 Penicillium expansum Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000005068 cooling lubricant Substances 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- FMPCLQRDPGBIAT-UHFFFAOYSA-N 1,5-dichloro-1,5-bis(4-methylphenyl)pentan-3-one Chemical compound C1=CC(C)=CC=C1C(Cl)CC(=O)CC(Cl)C1=CC=C(C)C=C1 FMPCLQRDPGBIAT-UHFFFAOYSA-N 0.000 description 1
- LYJQMHVYFFZQGY-UHFFFAOYSA-N 1,5-dichloropentan-3-one Chemical compound ClCCC(=O)CCCl LYJQMHVYFFZQGY-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 description 1
- DZHDMKXJJCFOGT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2h-1,3-thiazin-2-amine;hydrochloride Chemical compound Cl.NC1SC=CC(C=2C(=CC(Cl)=CC=2)Cl)=N1 DZHDMKXJJCFOGT-UHFFFAOYSA-N 0.000 description 1
- RRUUBVVPYHBZNU-UHFFFAOYSA-N 4-(4-methylphenyl)-2h-1,3-thiazin-2-amine Chemical compound C1=CC(C)=CC=C1C1=NC(N)SC=C1 RRUUBVVPYHBZNU-UHFFFAOYSA-N 0.000 description 1
- KUILJDVETVEZMK-UHFFFAOYSA-N 4-(4-methylphenyl)-n-naphthalen-2-yl-2h-1,3-thiazin-2-amine Chemical compound C1=CC(C)=CC=C1C(C=CS1)=NC1NC1=CC=C(C=CC=C2)C2=C1 KUILJDVETVEZMK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- ULOUJZDTBMCSHG-UHFFFAOYSA-N 4-naphthalen-1-yl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ULOUJZDTBMCSHG-UHFFFAOYSA-N 0.000 description 1
- MFPPVWVNLMINHH-UHFFFAOYSA-N 4-phenyl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C=CC=CC=2)=N1 MFPPVWVNLMINHH-UHFFFAOYSA-N 0.000 description 1
- LZRSVSKSQCLAMV-UHFFFAOYSA-N 4-thiophen-2-yl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2SC=CC=2)=N1 LZRSVSKSQCLAMV-UHFFFAOYSA-N 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 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 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XGHYAFHQCSCJTD-UHFFFAOYSA-N n-methyl-4-(4-methylphenyl)-2h-1,3-thiazin-2-amine Chemical compound CNC1SC=CC(C=2C=CC(C)=CC=2)=N1 XGHYAFHQCSCJTD-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 238000005866 tritylation reaction Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2426653A DE2426653C3 (de) | 1974-06-01 | 1974-06-01 | Derivate des 2-Amino-1,3-thiazins |
| DE2426653 | 1974-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS511482A JPS511482A (en) | 1976-01-08 |
| JPS5913516B2 true JPS5913516B2 (ja) | 1984-03-30 |
Family
ID=5917110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50063556A Expired JPS5913516B2 (ja) | 1974-06-01 | 1975-05-29 | 新規２−アミノ−１，３−チアジン類の製造方法 |
Country Status (19)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4210545A (en) * | 1979-03-30 | 1980-07-01 | Standard Oil Company (Indiana) | Oxidation resistant lubricant composition |
| EP2612854B1 (en) | 2005-10-25 | 2015-04-29 | Shionogi&Co., Ltd. | Aminothiazolidine and aminotetrahydrothiazepine derivatives as BACE 1 inhibitors |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| WO2008133274A1 (ja) | 2007-04-24 | 2008-11-06 | Shionogi & Co., Ltd. | 環式基で置換されたアミノジヒドロチアジン誘導体 |
| MY153621A (en) | 2008-06-13 | 2015-02-27 | Shionogi & Co | Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity |
| ES2590038T5 (es) | 2009-12-11 | 2021-10-19 | Shionogi & Co | Derivado de oxazina |
| EP2634188A4 (en) | 2010-10-29 | 2014-05-07 | Shionogi & Co | FUSIONED AMINODIHYDROPYRIMIDINE DERIVATIVE |
| JP5816630B2 (ja) | 2010-10-29 | 2015-11-18 | 塩野義製薬株式会社 | ナフチリジン誘導体 |
| CN103608345A (zh) | 2011-04-26 | 2014-02-26 | 盐野义制药株式会社 | 噁嗪衍生物和含有该噁嗪衍生物的bace1抑制剂 |
| US9540359B2 (en) | 2012-10-24 | 2017-01-10 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having BACE1 inhibitory activity |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228935A (en) * | 1966-01-11 | Novel z-phenylamino-xh-s,g-dihydro-i,j- thiazine derivatives | ||
| DE1159953B (de) * | 1960-07-23 | 1963-12-27 | Albert Ag Chem Werke | Verfahren zur Herstellung von 2-Imino-1, 2, 3, 6-tetrahydro-1, 3-thiazinderivaten |
-
1974
- 1974-06-01 DE DE2426653A patent/DE2426653C3/de not_active Expired
-
1975
- 1975-05-09 GB GB1962675A patent/GB1452448A/en not_active Expired
- 1975-05-16 NO NO751760A patent/NO751760L/no unknown
- 1975-05-28 US US05/581,526 patent/US4049807A/en not_active Expired - Lifetime
- 1975-05-28 IL IL47373A patent/IL47373A/en unknown
- 1975-05-29 BE BE156844A patent/BE829654A/xx unknown
- 1975-05-29 FI FI751581A patent/FI751581A7/fi not_active Application Discontinuation
- 1975-05-29 SE SE7506150A patent/SE7506150L/xx unknown
- 1975-05-29 JP JP50063556A patent/JPS5913516B2/ja not_active Expired
- 1975-05-30 IT IT49840/75A patent/IT1040613B/it active
- 1975-05-30 LU LU72620A patent/LU72620A1/xx unknown
- 1975-05-30 BR BR4366/75D patent/BR7503410A/pt unknown
- 1975-05-30 IE IE1208/75A patent/IE41151B1/xx unknown
- 1975-05-30 CH CH700775A patent/CH576968A5/xx not_active IP Right Cessation
- 1975-05-30 NL NL7506472.A patent/NL163511C/xx not_active IP Right Cessation
- 1975-05-30 DK DK244775A patent/DK244775A/da unknown
- 1975-05-30 AT AT411875A patent/AT344447B/de not_active IP Right Cessation
- 1975-05-30 FR FR7516899A patent/FR2275466A1/fr active Granted
- 1975-05-30 ES ES438044A patent/ES438044A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2426653B2 (de) | 1981-07-02 |
| IE41151L (en) | 1975-12-01 |
| NO751760L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-02 |
| BE829654A (fr) | 1975-12-01 |
| FI751581A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-02 |
| IL47373A (en) | 1977-11-30 |
| FR2275466A1 (fr) | 1976-01-16 |
| LU72620A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-17 |
| NL163511C (nl) | 1980-09-15 |
| NL163511B (nl) | 1980-04-15 |
| US4049807A (en) | 1977-09-20 |
| BR7503410A (pt) | 1976-05-25 |
| DE2426653C3 (de) | 1982-05-06 |
| SE7506150L (sv) | 1975-12-02 |
| ES438044A1 (es) | 1977-01-16 |
| CH576968A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-30 |
| ATA411875A (de) | 1977-11-15 |
| DK244775A (da) | 1975-12-02 |
| GB1452448A (en) | 1976-10-13 |
| FR2275466B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-01-19 |
| NL7506472A (nl) | 1975-12-03 |
| IT1040613B (it) | 1979-12-20 |
| IE41151B1 (en) | 1979-10-24 |
| IL47373A0 (en) | 1975-07-28 |
| JPS511482A (en) | 1976-01-08 |
| AT344447B (de) | 1978-07-25 |
| DE2426653A1 (de) | 1975-12-04 |
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