DE2147025A1 - Neue mesoionische 1,3,4-thiadiazolimin-(5)-derivate und ein verfahren zu ihrer herstellung - Google Patents
Neue mesoionische 1,3,4-thiadiazolimin-(5)-derivate und ein verfahren zu ihrer herstellungInfo
- Publication number
- DE2147025A1 DE2147025A1 DE2147025A DE2147025A DE2147025A1 DE 2147025 A1 DE2147025 A1 DE 2147025A1 DE 2147025 A DE2147025 A DE 2147025A DE 2147025 A DE2147025 A DE 2147025A DE 2147025 A1 DE2147025 A1 DE 2147025A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- mesoionic
- derivatives
- thiadiazolimine
- acid
- 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.)
- Pending
Links
- MEVCOHCAOWTMQD-UHFFFAOYSA-N N=S1C=NN=C1 Chemical compound N=S1C=NN=C1 MEVCOHCAOWTMQD-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 acyl isothiocyanates Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 150000001727 carbonic acid monoesters Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- HAFZLXFHOHWQTH-UHFFFAOYSA-N 3-methyl-2-phenyl-2h-1,3,4-thiadiazole Chemical compound CN1N=CSC1C1=CC=CC=C1 HAFZLXFHOHWQTH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 238000010792 warming Methods 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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2147025A DE2147025A1 (de) | 1971-09-21 | 1971-09-21 | Neue mesoionische 1,3,4-thiadiazolimin-(5)-derivate und ein verfahren zu ihrer herstellung |
| CA151434A CA986523A (en) | 1971-09-21 | 1972-09-11 | Mesoionic 1,3,4-thiadiazolimino-(5) derivatives and a process for their production |
| US288124A US3884930A (en) | 1971-09-21 | 1972-09-11 | Mesoionic 2,3-substituted 5-acylimino-1,3,4-thiadiazoles |
| SE7212037A SE379200B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-21 | 1972-09-18 | |
| CH1368272A CH605869A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-21 | 1972-09-19 | |
| FR7233118A FR2154530B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-21 | 1972-09-19 | |
| AT804372A AT316547B (de) | 1971-09-21 | 1972-09-20 | Verfahren zur Herstellung neuer mesoionischer 1,3,4-Thiadiazolimin-(5)-Derivate und ihrer Salze |
| JP47093789A JPS4836173A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-21 | 1972-09-20 | |
| GB4347972A GB1400547A (en) | 1971-09-21 | 1972-09-20 | Mesoionic 1,3,4-thiadiazolimino-5-derivatives and a process for their production |
| NL7212791A NL7212791A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-09-21 | 1972-09-21 | |
| BE789088A BE789088A (fr) | 1971-09-21 | 1972-09-21 | Derives meso-ioniques de la 1,3,4-thiadiazole-imine-(5), leur preparation et leurs utilisations therapeutiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2147025A DE2147025A1 (de) | 1971-09-21 | 1971-09-21 | Neue mesoionische 1,3,4-thiadiazolimin-(5)-derivate und ein verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2147025A1 true DE2147025A1 (de) | 1973-03-29 |
Family
ID=5820128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2147025A Pending DE2147025A1 (de) | 1971-09-21 | 1971-09-21 | Neue mesoionische 1,3,4-thiadiazolimin-(5)-derivate und ein verfahren zu ihrer herstellung |
Country Status (11)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2408288A1 (de) * | 1974-02-21 | 1975-09-04 | Basf Ag | Neue anhydro-2-mercapto-1,3,4-thiadiazoliumhydroxide |
| CN114605352A (zh) * | 2022-04-22 | 2022-06-10 | 江苏海洋大学 | 含1,3,4-噻二唑酰胺的没食子酸类衍生物及制法与用途 |
| CN116693466A (zh) * | 2023-06-08 | 2023-09-05 | 江苏海洋大学 | 含噻唑结构的没食子酸类衍生物及其的合成方法与用途 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3941927A (en) * | 1974-11-11 | 1976-03-02 | Battelle Development Corporation | Optical fiber deflection device |
| JPS595896B2 (ja) * | 1977-06-15 | 1984-02-07 | エプソン株式会社 | 残像効果型表示装置 |
| CN114507194A (zh) * | 2020-11-17 | 2022-05-17 | 天津科技大学 | 一种5-取代-1,3,4-噻二唑酰胺类衍生物及其制备方法和应用 |
| CN117069679B (zh) * | 2023-07-11 | 2025-08-08 | 湖南省农业生物技术研究所 | 一种n-(取代苯基)噻唑苯氧乙酰胺类化合物及其制备方法与应用 |
-
1971
- 1971-09-21 DE DE2147025A patent/DE2147025A1/de active Pending
-
1972
- 1972-09-11 US US288124A patent/US3884930A/en not_active Expired - Lifetime
- 1972-09-11 CA CA151434A patent/CA986523A/en not_active Expired
- 1972-09-18 SE SE7212037A patent/SE379200B/xx unknown
- 1972-09-19 CH CH1368272A patent/CH605869A5/xx not_active IP Right Cessation
- 1972-09-19 FR FR7233118A patent/FR2154530B1/fr not_active Expired
- 1972-09-20 AT AT804372A patent/AT316547B/de not_active IP Right Cessation
- 1972-09-20 JP JP47093789A patent/JPS4836173A/ja active Pending
- 1972-09-20 GB GB4347972A patent/GB1400547A/en not_active Expired
- 1972-09-21 NL NL7212791A patent/NL7212791A/xx not_active Application Discontinuation
- 1972-09-21 BE BE789088A patent/BE789088A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2408288A1 (de) * | 1974-02-21 | 1975-09-04 | Basf Ag | Neue anhydro-2-mercapto-1,3,4-thiadiazoliumhydroxide |
| CN114605352A (zh) * | 2022-04-22 | 2022-06-10 | 江苏海洋大学 | 含1,3,4-噻二唑酰胺的没食子酸类衍生物及制法与用途 |
| CN114605352B (zh) * | 2022-04-22 | 2023-04-25 | 江苏海洋大学 | 含1,3,4-噻二唑酰胺的没食子酸类衍生物及制法与用途 |
| CN116693466A (zh) * | 2023-06-08 | 2023-09-05 | 江苏海洋大学 | 含噻唑结构的没食子酸类衍生物及其的合成方法与用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2154530B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-08 |
| JPS4836173A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-28 |
| GB1400547A (en) | 1975-07-16 |
| SE379200B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-29 |
| CA986523A (en) | 1976-03-30 |
| BE789088A (fr) | 1973-03-21 |
| US3884930A (en) | 1975-05-20 |
| FR2154530A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-11 |
| AT316547B (de) | 1974-07-10 |
| NL7212791A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-03-23 |
| CH605869A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |