SU649320A3 - Способ получени эфиров 2-(диметилкарбамоилимино)-1,3,4-тиадиазолин 3-карбоновой кислоты - Google Patents
Способ получени эфиров 2-(диметилкарбамоилимино)-1,3,4-тиадиазолин 3-карбоновой кислотыInfo
- Publication number
- SU649320A3 SU649320A3 SU772468202A SU2468202A SU649320A3 SU 649320 A3 SU649320 A3 SU 649320A3 SU 772468202 A SU772468202 A SU 772468202A SU 2468202 A SU2468202 A SU 2468202A SU 649320 A3 SU649320 A3 SU 649320A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxylic acid
- dimethylcarbamoylimino
- ester
- thiadiazoline
- thiadiazolin
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 4
- PNWXIVHAFKHCRF-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC=NN1C(=O)O)C PNWXIVHAFKHCRF-UHFFFAOYSA-N 0.000 title 1
- -1 tertiary amines Chemical class 0.000 description 72
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QXNWEVRWCGCWDC-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-ethylsulfonyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound C(C)S(=O)(=O)C1=NN(C(S1)=NC(N(C)C)=O)C(=O)O QXNWEVRWCGCWDC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QDWYHFRTJNLKGU-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SC)C QDWYHFRTJNLKGU-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PFXWXVDBAIXSCP-UHFFFAOYSA-N 1,1-dimethyl-3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)urea Chemical compound CSC1=NN=C(NC(=O)N(C)C)S1 PFXWXVDBAIXSCP-UHFFFAOYSA-N 0.000 description 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
- LXOWVWRJUZBLTC-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfanyl)-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SCC(C)C)C LXOWVWRJUZBLTC-UHFFFAOYSA-N 0.000 description 1
- ZLHPPWWAIANLOB-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-ethylsulfanyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound C(C)SC1=NN(C(S1)=NC(N(C)C)=O)C(=O)O ZLHPPWWAIANLOB-UHFFFAOYSA-N 0.000 description 1
- FPXKRZGYVWONIX-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-hexylsulfanyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SCCCCCC)C FPXKRZGYVWONIX-UHFFFAOYSA-N 0.000 description 1
- DKCPUBONIIWSMH-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfanyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SC(C)C)C DKCPUBONIIWSMH-UHFFFAOYSA-N 0.000 description 1
- CISOIRUDFTUDFO-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)S(=O)(=O)C(C)C)C CISOIRUDFTUDFO-UHFFFAOYSA-N 0.000 description 1
- AYLWYVAKWIUMPJ-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CC(C)COC(=O)N1N=C(S(C)(=O)=O)SC1=NC(=O)N(C)C AYLWYVAKWIUMPJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- PKZYLZYTIAANMV-UHFFFAOYSA-N 5-butylsulfanyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylic acid Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SCCCC)C PKZYLZYTIAANMV-UHFFFAOYSA-N 0.000 description 1
- PJOSMWUYCDZGBL-UHFFFAOYSA-N CN(C(=O)N=C1SC(=NN1C(=O)O)SCC=CC)C Chemical compound CN(C(=O)N=C1SC(=NN1C(=O)O)SCC=CC)C PJOSMWUYCDZGBL-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VXHCZOQTDNVASO-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-(2-methylpropylsulfonyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CC(C)C)=NC(N(C)C)=O VXHCZOQTDNVASO-UHFFFAOYSA-N 0.000 description 1
- DOUXLYWKNBLYRU-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfinyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)CCCCCC)=NC(N(C)C)=O DOUXLYWKNBLYRU-UHFFFAOYSA-N 0.000 description 1
- YFXPCVAXBXYKPG-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-hexylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCCCC)=NC(N(C)C)=O YFXPCVAXBXYKPG-UHFFFAOYSA-N 0.000 description 1
- FFYAKFBZVMKTCP-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-5-propan-2-ylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)C(C)C)=NC(N(C)C)=O FFYAKFBZVMKTCP-UHFFFAOYSA-N 0.000 description 1
- MMZCPCKRLGYQJR-UHFFFAOYSA-N butyl 5-butylsulfonyl-2-(dimethylcarbamoylimino)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CCC)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCC)=NC(N(C)C)=O MMZCPCKRLGYQJR-UHFFFAOYSA-N 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HPFKTUCCYFEKFI-UHFFFAOYSA-N ethyl 2-(dimethylcarbamoylimino)-5-hexylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)OC(=O)N1C(SC(=N1)S(=O)(=O)CCCCCC)=NC(N(C)C)=O HPFKTUCCYFEKFI-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LZJZKPWZKHFBTC-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-5-prop-2-enylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound COC(=O)N1N=C(SCC=C)SC1=NC(=O)N(C)C LZJZKPWZKHFBTC-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NCAZTGMXEIWTHQ-UHFFFAOYSA-N phenyl 2-(dimethylcarbamoylimino)-5-methylsulfanyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC(SC)=NN1C(=O)OC1=CC=CC=C1 NCAZTGMXEIWTHQ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ABZMLLKVVODUGL-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC(S(C)(=O)=O)=NN1C(=O)OCC=C ABZMLLKVVODUGL-UHFFFAOYSA-N 0.000 description 1
- MPGDMWCVIWYLSI-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-5-methylsulfonyl-1,3,4-thiadiazole-3-carboxylate Chemical compound C(C)(C)OC(=O)N1C(SC(=N1)S(=O)(=O)C)=NC(N(C)C)=O MPGDMWCVIWYLSI-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- HFMURDFBAPHSKY-UHFFFAOYSA-N propyl 2-(dimethylcarbamoylimino)-5-(2-methylprop-2-enylsulfanyl)-1,3,4-thiadiazole-3-carboxylate Chemical compound C(CC)OC(=O)N1C(SC(=N1)SCC(=C)C)=NC(N(C)C)=O HFMURDFBAPHSKY-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940086542 triethylamine Drugs 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621647 DE2621647A1 (de) | 1976-05-13 | 1976-05-13 | 2-(dimethylcarbamoylimino)-1,3,4- thiadiazolin-3-carbonsaeure-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU649320A3 true SU649320A3 (ru) | 1979-02-25 |
Family
ID=5978046
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772468202A SU649320A3 (ru) | 1976-05-13 | 1977-04-12 | Способ получени эфиров 2-(диметилкарбамоилимино)-1,3,4-тиадиазолин 3-карбоновой кислоты |
| SU772475610A SU648048A3 (ru) | 1976-05-13 | 1977-04-28 | Гербицидное средство |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772475610A SU648048A3 (ru) | 1976-05-13 | 1977-04-28 | Гербицидное средство |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4169718A (enExample) |
| JP (1) | JPS52139062A (enExample) |
| AT (1) | AT354802B (enExample) |
| AU (1) | AU2513377A (enExample) |
| BE (1) | BE854614A (enExample) |
| BG (1) | BG27716A3 (enExample) |
| CA (1) | CA1090808A (enExample) |
| CS (1) | CS192480B2 (enExample) |
| DD (1) | DD130201A5 (enExample) |
| DE (1) | DE2621647A1 (enExample) |
| DK (1) | DK114477A (enExample) |
| ES (1) | ES457730A1 (enExample) |
| FI (1) | FI771298A7 (enExample) |
| FR (1) | FR2351110A1 (enExample) |
| GB (1) | GB1583271A (enExample) |
| GR (1) | GR63745B (enExample) |
| IE (1) | IE45053B1 (enExample) |
| IL (1) | IL52033A (enExample) |
| IT (1) | IT1085078B (enExample) |
| LU (1) | LU76938A1 (enExample) |
| NL (1) | NL7703889A (enExample) |
| NO (1) | NO771675L (enExample) |
| PL (1) | PL102602B1 (enExample) |
| PT (1) | PT66533B (enExample) |
| RO (1) | RO72224A (enExample) |
| SE (1) | SE7705508L (enExample) |
| SU (2) | SU649320A3 (enExample) |
| TR (1) | TR19696A (enExample) |
| ZA (1) | ZA772869B (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293262A (enExample) * | 1962-05-28 | |||
| DE2124260A1 (de) * | 1971-05-15 | 1972-11-30 | Farbenfabriken Bayer AG, 5090 Le verkusen | Verfahren zur Herstellung von 4 sub stituierten 1,3,4 Thiadiazolon (5) yl (2) harnstoffen |
-
1976
- 1976-05-13 DE DE19762621647 patent/DE2621647A1/de not_active Withdrawn
-
1977
- 1977-03-11 LU LU76938A patent/LU76938A1/xx unknown
- 1977-03-16 DK DK114477A patent/DK114477A/da unknown
- 1977-03-18 CS CS771820A patent/CS192480B2/cs unknown
- 1977-04-07 NL NL7703889A patent/NL7703889A/xx not_active Application Discontinuation
- 1977-04-12 SU SU772468202A patent/SU649320A3/ru active
- 1977-04-12 ES ES457730A patent/ES457730A1/es not_active Expired
- 1977-04-25 FI FI771298A patent/FI771298A7/fi not_active Application Discontinuation
- 1977-04-26 BG BG036125A patent/BG27716A3/xx unknown
- 1977-04-28 SU SU772475610A patent/SU648048A3/ru active
- 1977-05-02 GB GB18232/77A patent/GB1583271A/en not_active Expired
- 1977-05-05 IL IL52033A patent/IL52033A/xx unknown
- 1977-05-06 IE IE928/77A patent/IE45053B1/en unknown
- 1977-05-07 RO RO7790253A patent/RO72224A/ro unknown
- 1977-05-10 TR TR19696A patent/TR19696A/xx unknown
- 1977-05-10 US US05/795,642 patent/US4169718A/en not_active Expired - Lifetime
- 1977-05-11 DD DD7700198870A patent/DD130201A5/xx unknown
- 1977-05-11 SE SE7705508A patent/SE7705508L/xx unknown
- 1977-05-11 PL PL1977198027A patent/PL102602B1/pl unknown
- 1977-05-11 AT AT336177A patent/AT354802B/de not_active IP Right Cessation
- 1977-05-11 PT PT66533A patent/PT66533B/pt unknown
- 1977-05-11 GR GR53442A patent/GR63745B/el unknown
- 1977-05-12 IT IT23469/77A patent/IT1085078B/it active
- 1977-05-12 NO NO771675A patent/NO771675L/no unknown
- 1977-05-12 CA CA278,440A patent/CA1090808A/en not_active Expired
- 1977-05-13 ZA ZA00772869A patent/ZA772869B/xx unknown
- 1977-05-13 JP JP5523377A patent/JPS52139062A/ja active Granted
- 1977-05-13 FR FR7714692A patent/FR2351110A1/fr active Pending
- 1977-05-13 AU AU25133/77A patent/AU2513377A/en not_active Expired
- 1977-05-13 BE BE177559A patent/BE854614A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU76938A1 (enExample) | 1977-07-14 |
| JPS5538342B2 (enExample) | 1980-10-03 |
| NL7703889A (nl) | 1977-11-15 |
| ATA336177A (de) | 1979-06-15 |
| IL52033A (en) | 1980-03-31 |
| IL52033A0 (en) | 1977-07-31 |
| ES457730A1 (es) | 1978-02-16 |
| GB1583271A (en) | 1981-01-21 |
| IE45053L (en) | 1977-11-13 |
| BG27716A3 (bg) | 1979-12-12 |
| DK114477A (da) | 1977-11-14 |
| NO771675L (no) | 1977-11-15 |
| DE2621647A1 (de) | 1977-12-01 |
| US4169718A (en) | 1979-10-02 |
| ZA772869B (en) | 1978-03-29 |
| PL102602B1 (pl) | 1979-04-30 |
| JPS52139062A (en) | 1977-11-19 |
| FR2351110A1 (fr) | 1977-12-09 |
| SE7705508L (sv) | 1977-11-14 |
| AU2513377A (en) | 1978-11-16 |
| DD130201A5 (de) | 1978-03-15 |
| SU648048A3 (ru) | 1979-02-15 |
| CS192480B2 (en) | 1979-08-31 |
| PT66533B (de) | 1978-10-17 |
| IE45053B1 (en) | 1982-06-16 |
| PL198027A1 (pl) | 1978-02-13 |
| TR19696A (tr) | 1979-10-11 |
| FI771298A7 (enExample) | 1977-11-14 |
| RO72224A (ro) | 1982-05-10 |
| AT354802B (de) | 1979-01-25 |
| BE854614A (fr) | 1977-11-14 |
| PT66533A (de) | 1977-06-01 |
| GR63745B (en) | 1979-12-04 |
| CA1090808A (en) | 1980-12-02 |
| IT1085078B (it) | 1985-05-28 |
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