HU182999B - Process for producing 1,2,3-thiadiazol-5-yl-urea derivatives - Google Patents
Process for producing 1,2,3-thiadiazol-5-yl-urea derivatives Download PDFInfo
- Publication number
- HU182999B HU182999B HU79SCHE691A HUSC000691A HU182999B HU 182999 B HU182999 B HU 182999B HU 79SCHE691 A HU79SCHE691 A HU 79SCHE691A HU SC000691 A HUSC000691 A HU SC000691A HU 182999 B HU182999 B HU 182999B
- Authority
- HU
- Hungary
- Prior art keywords
- thiadiazol
- methyl
- formula
- pyridyl
- thiadiazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- HQYZTGGAEAFKIO-UHFFFAOYSA-N thiadiazol-5-ylurea Chemical class NC(=O)NC1=CN=NS1 HQYZTGGAEAFKIO-UHFFFAOYSA-N 0.000 title claims description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- UDSVLKOSDHNDNJ-UHFFFAOYSA-N thiadiazole-5-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CN=NS1 UDSVLKOSDHNDNJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- -1 2-isopropylphenyl Chemical group 0.000 claims description 60
- 150000001540 azides Chemical class 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 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
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000004202 carbamide Substances 0.000 description 13
- 235000013877 carbamide Nutrition 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 3
- DHTBORBAEQJWLZ-UHFFFAOYSA-N thiadiazole-5-carbohydrazide Chemical compound NNC(=O)C1=CN=NS1 DHTBORBAEQJWLZ-UHFFFAOYSA-N 0.000 description 3
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010029897 Obsessive thoughts Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229950001336 bromamide Drugs 0.000 description 2
- 150000001731 carboxylic acid azides Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GDPRTNRLCIICFQ-UHFFFAOYSA-N thiadiazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=NS1 GDPRTNRLCIICFQ-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RPOZCTAHYSTBLD-UHFFFAOYSA-N 1-(2-methylphenyl)-3-(thiadiazol-5-yl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CN=NS1 RPOZCTAHYSTBLD-UHFFFAOYSA-N 0.000 description 1
- OYGNTCAUKJDXRJ-UHFFFAOYSA-N 1-(3-nitrophenyl)-3-(thiadiazol-5-yl)urea Chemical compound [O-][N+](=O)C1=CC=CC(NC(=O)NC=2SN=NC=2)=C1 OYGNTCAUKJDXRJ-UHFFFAOYSA-N 0.000 description 1
- ZJWYOQHBYMIWKB-UHFFFAOYSA-N 1-(4-methylpyridin-2-yl)-3-(thiadiazol-5-yl)urea Chemical compound CC1=CC=NC(NC(=O)NC=2SN=NC=2)=C1 ZJWYOQHBYMIWKB-UHFFFAOYSA-N 0.000 description 1
- MZOOBLSBLICSGJ-UHFFFAOYSA-N 1-benzyl-3-(thiadiazol-5-yl)urea Chemical compound C=1N=NSC=1NC(=O)NCC1=CC=CC=C1 MZOOBLSBLICSGJ-UHFFFAOYSA-N 0.000 description 1
- RVDLYINGZRXPIQ-UHFFFAOYSA-N 1-butyl-1-phenyl-3-(thiadiazol-5-yl)urea Chemical compound C=1C=CC=CC=1N(CCCC)C(=O)NC1=CN=NS1 RVDLYINGZRXPIQ-UHFFFAOYSA-N 0.000 description 1
- WPLACKGYQTURBS-UHFFFAOYSA-N 1-methyl-3-(thiadiazol-5-yl)urea Chemical compound CNC(=O)NC1=CN=NS1 WPLACKGYQTURBS-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FXAVHKREGHKQAW-UHFFFAOYSA-N CC(C)N(C1=CC=CC=C1)C(=O)NC2=CN=NS2 Chemical compound CC(C)N(C1=CC=CC=C1)C(=O)NC2=CN=NS2 FXAVHKREGHKQAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- YKQNEBMYFBXDSV-UHFFFAOYSA-O NC(N[S+]1N=NC=C1)=O Chemical compound NC(N[S+]1N=NC=C1)=O YKQNEBMYFBXDSV-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZGJIPMGEIQGQID-UHFFFAOYSA-N thiadiazole-4-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CSN=N1 ZGJIPMGEIQGQID-UHFFFAOYSA-N 0.000 description 1
- SZGOQYAJFJBSQD-UHFFFAOYSA-N thiadiazole-5-carboxamide Chemical compound NC(=O)C1=CN=NS1 SZGOQYAJFJBSQD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000008096 xylene Substances 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
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841825 DE2841825A1 (de) | 1978-09-22 | 1978-09-22 | Verfahren zur herstellung von 1,2,3- thiadiazol-5-yl-harnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182999B true HU182999B (en) | 1984-03-28 |
Family
ID=6050477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79SCHE691A HU182999B (en) | 1978-09-22 | 1979-09-21 | Process for producing 1,2,3-thiadiazol-5-yl-urea derivatives |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5545683A (cs) |
| AR (1) | AR223349A1 (cs) |
| AT (1) | AT373593B (cs) |
| AU (1) | AU533137B2 (cs) |
| BE (1) | BE878925A (cs) |
| BG (1) | BG30930A3 (cs) |
| BR (1) | BR7905614A (cs) |
| CA (1) | CA1131224A (cs) |
| CH (1) | CH641792A5 (cs) |
| CS (1) | CS209936B2 (cs) |
| DD (1) | DD146184A5 (cs) |
| DE (1) | DE2841825A1 (cs) |
| DK (1) | DK361579A (cs) |
| EG (1) | EG14167A (cs) |
| ES (1) | ES483788A1 (cs) |
| FI (1) | FI69838C (cs) |
| FR (1) | FR2436783A1 (cs) |
| GB (1) | GB2031889B (cs) |
| GR (1) | GR73092B (cs) |
| HU (1) | HU182999B (cs) |
| IE (1) | IE48944B1 (cs) |
| IL (1) | IL58274A (cs) |
| IT (1) | IT1123731B (cs) |
| LU (1) | LU81704A1 (cs) |
| NL (1) | NL7905355A (cs) |
| NZ (1) | NZ191603A (cs) |
| PH (1) | PH15388A (cs) |
| PL (1) | PL123956B1 (cs) |
| PT (1) | PT70178A (cs) |
| RO (1) | RO77754A (cs) |
| SE (1) | SE435376B (cs) |
| SU (1) | SU921466A3 (cs) |
| TR (1) | TR20895A (cs) |
| YU (1) | YU40759B (cs) |
| ZA (1) | ZA794722B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2909991A1 (de) * | 1979-03-12 | 1980-10-02 | Schering Ag | 1,2,3-thiadiazol-5-carbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und wuchsregulatorischer sowie fungizider wirkung |
| JPS55150238U (cs) * | 1980-04-03 | 1980-10-29 | ||
| DE3139506A1 (de) * | 1981-10-01 | 1983-04-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 1,2,3-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD103124A5 (cs) | 1972-03-23 | 1974-01-12 | ||
| DE2636994C2 (de) | 1976-08-13 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 5-Amino-1,2,3-thiadiazol |
-
1978
- 1978-09-22 DE DE19782841825 patent/DE2841825A1/de not_active Withdrawn
-
1979
- 1979-07-09 NL NL7905355A patent/NL7905355A/nl not_active Application Discontinuation
- 1979-08-20 YU YU2027/79A patent/YU40759B/xx unknown
- 1979-08-29 DK DK361579A patent/DK361579A/da not_active Application Discontinuation
- 1979-08-31 ES ES483788A patent/ES483788A1/es not_active Expired
- 1979-08-31 BR BR7905614A patent/BR7905614A/pt unknown
- 1979-09-06 FI FI792770A patent/FI69838C/fi not_active IP Right Cessation
- 1979-09-06 ZA ZA00794722A patent/ZA794722B/xx unknown
- 1979-09-11 CA CA335,363A patent/CA1131224A/en not_active Expired
- 1979-09-14 PT PT70178A patent/PT70178A/pt unknown
- 1979-09-14 BG BG044862A patent/BG30930A3/xx unknown
- 1979-09-17 TR TR20895A patent/TR20895A/xx unknown
- 1979-09-18 EG EG555/79A patent/EG14167A/xx active
- 1979-09-18 NZ NZ191603A patent/NZ191603A/xx unknown
- 1979-09-19 IL IL58274A patent/IL58274A/xx unknown
- 1979-09-19 DD DD215645A patent/DD146184A5/de unknown
- 1979-09-20 CH CH850479A patent/CH641792A5/de not_active IP Right Cessation
- 1979-09-20 PH PH23049A patent/PH15388A/en unknown
- 1979-09-20 IT IT25880/79A patent/IT1123731B/it active
- 1979-09-20 LU LU81704A patent/LU81704A1/de unknown
- 1979-09-20 GR GR60083A patent/GR73092B/el unknown
- 1979-09-20 PL PL1979218429A patent/PL123956B1/pl unknown
- 1979-09-20 SU SU792811707A patent/SU921466A3/ru active
- 1979-09-21 IE IE1789/79A patent/IE48944B1/en unknown
- 1979-09-21 RO RO7998731A patent/RO77754A/ro unknown
- 1979-09-21 AT AT0622779A patent/AT373593B/de not_active IP Right Cessation
- 1979-09-21 SE SE7907841A patent/SE435376B/sv not_active IP Right Cessation
- 1979-09-21 JP JP12093079A patent/JPS5545683A/ja active Pending
- 1979-09-21 CS CS796380A patent/CS209936B2/cs unknown
- 1979-09-21 AU AU51075/79A patent/AU533137B2/en not_active Ceased
- 1979-09-21 BE BE0/197257A patent/BE878925A/fr not_active IP Right Cessation
- 1979-09-21 AR AR278157A patent/AR223349A1/es active
- 1979-09-21 HU HU79SCHE691A patent/HU182999B/hu unknown
- 1979-09-21 GB GB7932815A patent/GB2031889B/en not_active Expired
- 1979-09-24 FR FR7923681A patent/FR2436783A1/fr active Granted
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