RU96101797A - SUBSTITUTED THIOPHENYL SULFONYLMUNE UTIES AND THIOPHENYL SULFONYLTIOMETRICS, METHOD OF THEIR RECEIVING, DRUG AND METHOD - Google Patents
SUBSTITUTED THIOPHENYL SULFONYLMUNE UTIES AND THIOPHENYL SULFONYLTIOMETRICS, METHOD OF THEIR RECEIVING, DRUG AND METHODInfo
- Publication number
- RU96101797A RU96101797A RU96101797/04A RU96101797A RU96101797A RU 96101797 A RU96101797 A RU 96101797A RU 96101797/04 A RU96101797/04 A RU 96101797/04A RU 96101797 A RU96101797 A RU 96101797A RU 96101797 A RU96101797 A RU 96101797A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- substituted
- atoms
- hydrogen
- thiophenesulfonylurea
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 2
- 229940079593 drugs Drugs 0.000 title claims 2
- DPEMFPKDEMIOMC-UHFFFAOYSA-N cyclohexa-2,4-diene-1-thione Chemical class S=C1CC=CC=[C]1 DPEMFPKDEMIOMC-UHFFFAOYSA-N 0.000 title 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- KLPPUPBECAHKEF-UHFFFAOYSA-N thiophen-2-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CS1 KLPPUPBECAHKEF-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- -1 tetraalkylammonium ions Chemical class 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- ARDGWQBDKKYVBM-UHFFFAOYSA-N thiophen-2-ylsulfonylthiourea Chemical compound NC(=S)NS(=O)(=O)C1=CC=CS1 ARDGWQBDKKYVBM-UHFFFAOYSA-N 0.000 claims 2
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical class OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims 1
- 206010007521 Cardiac arrhythmias Diseases 0.000 claims 1
- JBPHCEHVHVSGEP-UHFFFAOYSA-N N-(oxomethylidene)thiophene-2-sulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CS1 JBPHCEHVHVSGEP-UHFFFAOYSA-N 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N [N-]=C=S Chemical compound [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- NNHSFBDNDJBVBD-UHFFFAOYSA-N benzenesulfinylurea Chemical compound NC(=O)NS(=O)C1=CC=CC=C1 NNHSFBDNDJBVBD-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- IGXIQOFPTUWHFL-UHFFFAOYSA-N phenylsulfanylurea Chemical compound NC(=O)NSC1=CC=CC=C1 IGXIQOFPTUWHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229960001663 sulfanilamide Drugs 0.000 claims 1
- UVVUGWBBCDFNSD-UHFFFAOYSA-N tetraisocyanatosilane Chemical compound O=C=N[Si](N=C=O)(N=C=O)N=C=O UVVUGWBBCDFNSD-UHFFFAOYSA-N 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
Claims (1)
R(1) означает водород, галоген, алкил с 1 или 2 С-атомами, алкокси с 1 или 2 С-атомами, меркапталкил с 1 или 2 С-атомами, фторалкокси с 1 или 2 С-атомами, а также фторалкил с 1 или 2 С-атомами;
R(2) означает водород, метил или трифторметил;
Х - кислород (соединения 1а) или сера (соединения 1b);
Y, Z одинаковые или различные и означают водород, F, Cl, Br, I, алкил с 1 или 2 С-атомами, алкокси с 1 или 2 С-атомами;
2. Соединения формулы I по п.1, в которой
R(1) - водород или метил;
R(2) - водород, алкил с 1 или 2 С-атомами или алкокси с 1 или 2 С-атомами;
X - кислород или сера;
Y, Z - отличные друг от друга, фтор, хлор, метокси или алкокси.1. Substituted thiophenesulfonylurea and thiophenesulfonylurea of formula I
R (1) means hydrogen, halogen, alkyl with 1 or 2 C-atoms, alkoxy with 1 or 2 C-atoms, mercaptalkyl with 1 or 2 C-atoms, fluoroalkoxy with 1 or 2 C-atoms, and also fluoroalkyl with 1 or 2 carbon atoms;
R (2) is hydrogen, methyl, or trifluoromethyl;
X is oxygen (compounds 1a) or sulfur (compounds 1b);
Y, Z are the same or different and represent hydrogen, F, Cl, Br, I, alkyl with 1 or 2 C atoms, alkoxy with 1 or 2 C atoms;
2. The compounds of formula I according to claim 1, in which
R (1) is hydrogen or methyl;
R (2) is hydrogen, alkyl with 1 or 2 C-atoms or alkoxy with 1 or 2 C-atoms;
X is oxygen or sulfur;
Y, Z - different from each other, fluorine, chlorine, methoxy or alkoxy.
R(1) - водород или метил;
R(2) - водород или алкил с 1 или 2 С-атомами;
X - кислород;
Z, Y - отличные друг от друга, фтор, хлор, метокси или этокси.3. The compound of formula I according to claim 1, in which
R (1) is hydrogen or methyl;
R (2) is hydrogen or alkyl with 1 or 2 carbon atoms;
X is oxygen;
Z, Y - different from each other, fluorine, chlorine, methoxy or ethoxy.
R(1) - водород или метил;
R(2) - водород или алкил с 1 или 2 С-атомами;
X - сера;
Z, Y - отличные друг от друга, фтор, хлор, метокси или этокси.4. The compound of formula I according to claim 1, in which
R (1) is hydrogen or methyl;
R (2) is hydrogen or alkyl with 1 or 2 carbon atoms;
X is sulfur;
Z, Y - different from each other, fluorine, chlorine, methoxy or ethoxy.
(а) ароматический сульфонамид формулы II
или его соль формулы III
в которой R(1), Y и Z имеют указанные в п.1, значения и в которой М означают щелочные, щелочноземельные, аммониевые и тетраалкиламмониевые ионы, подвергают реакции преобразования до получения замещенных тиофенсульфонилмочевин I посредством R(2)-замещенных изоцианатов формулы IV)
R(2) - N = C = O,
в которой R(2) имеет вказанное в п.1 значение;
или (b) незамещенные теофенсульфонилмочевины Iа (R(2) = H) получают посредством преобразования ароматического тиофенсульфонамида формулы II или его соли III с помощью триалкилсилилизоцианата или тетраизоцианата кремния и расщепления первичных кремнийзамещенных тиофенсульфонилмочевин;
(с) тиофенсульфонилмочевину Iа
получают из ароматического тиофенсульфонамида II или его соли III в результате преобразования посредством R(2)-замещенного трихлорацетамида формулы V
в присутствии основания;
или (d) тиофенсульфонилмочевину Ib
получают из тиофенсульфонамида II
или его соли III
в результате реакции преобразования с помощью R(2)-замещенного изотиоцианата VI
R(1) - N = C = S
или замещенную тиофенсульфонилмочевину формулы Iа получают в результате превращения тиофенсульфонилтиомочевины структуры Ib;
или (f) тиофенсульфонилмочевину Iа получают из тиофенсульфонилгалогенида формулы VII
с помощью R(2)-замещенной мочевины или R(2)-замещенной бис(триалкилсилил) мочевины;
или (g) тиофенсульфонилмочевину Iа получают в результате реакции преобразования амина формулы R(2) - NH2 посредством тиофенсульфонилизоцианата формулы VIII
или (h) тиофенсульфонилтиомочевину Ib получают в результате преобразования амина формулы R(2) - NH2 посредством теофенсульфонил-изотиоцианата формулы IX
или (i) бензолсульфенилмочевину или бензолсульфинилмочевину окисляют до тиофенсульфонилмочевин Iа.5. The method of obtaining compound I according to claim 1, characterized in that
(a) aromatic sulfonamide of formula II
or its salt of formula III
in which R (1), Y and Z have the values specified in claim 1, and in which M denotes alkaline, alkaline earth, ammonium and tetraalkylammonium ions, is subjected to a conversion reaction to obtain substituted thiophenesulfonylureas I by R (2) -substituted isocyanates of the formula IV )
R (2) - N = C = O,
in which R (2) has the meaning indicated in claim 1;
or (b) unsubstituted theophenesulfonylurea Ia (R (2) = H) is obtained by converting an aromatic thiophenesulfonamide of formula II or its salt III with trialkylsilyl isocyanate or silicon tetraisocyanate and cleaving primary silicon-substituted thiophenesulfonylureas;
(c) thiophenesulfonylurea Ia
is obtained from aromatic thiophenesulfonamide II or its salt III as a result of conversion by R (2) -substituted trichloroacetamide of formula V
in the presence of a base;
or (d) thiophenesulfonylurea Ib
obtained from thiophenesulfonamide II
or its salts III
as a result of the conversion reaction using R (2) -substituted isothiocyanate VI
R (1) - N = C = S
or substituted thiophenesulfonylurea of formula Ia is obtained by converting thiophenesulfonylthiourea of structure Ib;
or (f) thiophenesulfonylurea Ia is obtained from a thiophenesulfonyl halide of formula VII
with R (2) -substituted urea or R (2) -substituted bis (trialkylsilyl) urea;
or (g) thiophenesulfonylurea Ia is obtained by converting an amine of formula R (2) - NH 2 with a thiophenesulfonyl isocyanate of formula VIII
or (h) thiophenesulfonyl thiourea Ib is obtained by converting an amine of the formula R (2) to NH 2 by a teofensulfonyl isothiocyanate of the formula IX
or (i) benzenesulfenyl urea or benzenesulfinyl urea is oxidized to thiophenesulfonylureas Ia.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19503136.9 | 1995-02-01 | ||
| DE19503136A DE19503136A1 (en) | 1995-02-01 | 1995-02-01 | Substituted thiophenylsulfonylureas and thioureas, processes for their preparation, their use as medicaments or diagnostic agents and medicaments containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96101797A true RU96101797A (en) | 1998-03-27 |
| RU2164916C2 RU2164916C2 (en) | 2001-04-10 |
Family
ID=7752837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96101797/04A RU2164916C2 (en) | 1995-02-01 | 1996-01-31 | Substituted thiophensulfonylureas, method of their synthesis and drug |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5792788A (en) |
| EP (1) | EP0729954B1 (en) |
| JP (1) | JP4021949B2 (en) |
| KR (1) | KR100449192B1 (en) |
| CN (1) | CN1071752C (en) |
| AR (1) | AR002026A1 (en) |
| AT (1) | ATE248829T1 (en) |
| AU (1) | AU700884B2 (en) |
| BR (1) | BR9600290A (en) |
| CA (1) | CA2168517C (en) |
| CZ (1) | CZ290738B6 (en) |
| DE (2) | DE19503136A1 (en) |
| DK (1) | DK0729954T3 (en) |
| ES (1) | ES2206525T3 (en) |
| FI (1) | FI120768B (en) |
| HR (1) | HRP960042B1 (en) |
| HU (1) | HU226121B1 (en) |
| IL (1) | IL116980A (en) |
| MY (1) | MY113423A (en) |
| NO (1) | NO315160B1 (en) |
| NZ (1) | NZ280890A (en) |
| PL (1) | PL183561B1 (en) |
| PT (1) | PT729954E (en) |
| RU (1) | RU2164916C2 (en) |
| SI (1) | SI9600033B (en) |
| SK (1) | SK284325B6 (en) |
| TR (1) | TR199600079A2 (en) |
| TW (1) | TW355184B (en) |
| ZA (1) | ZA96720B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004061017A1 (en) | 2004-12-18 | 2006-06-22 | Sanofi-Aventis Deutschland Gmbh | Piperidinesulfonylureas and thioureas, their preparation, their use and pharmaceutical compositions containing them |
| CN115703730A (en) * | 2021-08-16 | 2023-02-17 | 中国科学院上海药物研究所 | Sulfonylurea compound, preparation method and application thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124597A (en) * | 1964-03-10 | |||
| DE1493672C3 (en) * | 1964-08-01 | 1974-05-02 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Process for the preparation of benzenesulfonylureas |
| DE1518874C3 (en) * | 1964-10-07 | 1975-03-13 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Benzenesulfonylureas and process for their preparation |
| BE754588A (en) * | 1969-08-07 | 1971-02-08 | Hoechst Ag | THIOPHENE-SULFONYL-UREES AND THE MEDICINAL PRODUCTS CONTAINING THESE SUBSTANCES |
| DE2413514C3 (en) * | 1974-03-21 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | N-Acylaminoathylbenzenesulfonyl-N'-methylureas, process for their preparation and their use |
| EP0612724B1 (en) * | 1993-02-23 | 1996-12-27 | Hoechst Aktiengesellschaft | Substituted benzenesulfonylureas and -thioureas, process for their preparation and their use as pharmaceuticals |
| DE4341655A1 (en) * | 1993-12-07 | 1995-06-08 | Hoechst Ag | Amino-substituted benzenesulfonylureas and thioureas, processes for their preparation and their use as pharmaceuticals |
| DE4344957A1 (en) * | 1993-12-30 | 1995-07-06 | Hoechst Ag | Substituted benzenesulfonylureas and thioureas, production processes and possible uses of pharmaceutical preparations based on these compounds |
-
1995
- 1995-02-01 DE DE19503136A patent/DE19503136A1/en not_active Withdrawn
-
1996
- 1996-01-26 AT AT96101096T patent/ATE248829T1/en active
- 1996-01-26 PT PT96101096T patent/PT729954E/en unknown
- 1996-01-26 DE DE59610691T patent/DE59610691D1/en not_active Expired - Lifetime
- 1996-01-26 NZ NZ280890A patent/NZ280890A/en not_active IP Right Cessation
- 1996-01-26 ES ES96101096T patent/ES2206525T3/en not_active Expired - Lifetime
- 1996-01-26 EP EP96101096A patent/EP0729954B1/en not_active Expired - Lifetime
- 1996-01-26 DK DK96101096T patent/DK0729954T3/en active
- 1996-01-29 PL PL96312532A patent/PL183561B1/en not_active IP Right Cessation
- 1996-01-29 TW TW085101042A patent/TW355184B/en not_active IP Right Cessation
- 1996-01-29 HR HR960042A patent/HRP960042B1/en not_active IP Right Cessation
- 1996-01-30 TR TR96/00079A patent/TR199600079A2/en unknown
- 1996-01-30 AR ARP960101212A patent/AR002026A1/en active IP Right Grant
- 1996-01-30 FI FI960430A patent/FI120768B/en not_active IP Right Cessation
- 1996-01-30 CZ CZ1996280A patent/CZ290738B6/en not_active IP Right Cessation
- 1996-01-30 SK SK134-96A patent/SK284325B6/en not_active IP Right Cessation
- 1996-01-30 MY MYPI96000343A patent/MY113423A/en unknown
- 1996-01-30 CN CN96101109A patent/CN1071752C/en not_active Expired - Fee Related
- 1996-01-30 US US08/593,621 patent/US5792788A/en not_active Expired - Lifetime
- 1996-01-30 AU AU42246/96A patent/AU700884B2/en not_active Ceased
- 1996-01-31 HU HU9600218A patent/HU226121B1/en not_active IP Right Cessation
- 1996-01-31 BR BR9600290A patent/BR9600290A/en not_active IP Right Cessation
- 1996-01-31 RU RU96101797/04A patent/RU2164916C2/en not_active IP Right Cessation
- 1996-01-31 IL IL11698096A patent/IL116980A/en not_active IP Right Cessation
- 1996-01-31 NO NO19960411A patent/NO315160B1/en not_active IP Right Cessation
- 1996-01-31 CA CA002168517A patent/CA2168517C/en not_active Expired - Fee Related
- 1996-01-31 ZA ZA96720A patent/ZA96720B/en unknown
- 1996-01-31 JP JP01575996A patent/JP4021949B2/en not_active Expired - Lifetime
- 1996-02-01 SI SI9600033A patent/SI9600033B/en not_active IP Right Cessation
- 1996-02-01 KR KR1019960002405A patent/KR100449192B1/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60124411T8 (en) | IONIC LIQUIDS AND ITS USE AS SOLVENTS | |
| RU2002117428A (en) | Aminoheterocyclamides as pesticides and antiparasitic agents | |
| RU93058582A (en) | 2-PHENYLBENZO (B) FURANES AND - THIOPHENES AND METHOD FOR PRODUCING THEM | |
| RU98111769A (en) | Phenyl and Aminophenylalkyl Sulfonamide and Urea Derivatives | |
| AR241784A1 (en) | 2-(n-substituteguanidino)-4-hetero-arylthiazole antiulcer agents | |
| KR840000566A (en) | Preparation of 2-hydantoin and preparation method of herbicide using the same | |
| RU96102869A (en) | SUBSTITUTED BENZOLSULPHONYLMOLOVEVOI AND - THIOMOCHEVINA, METHOD FOR THEIR PRODUCTION, CONTAINING THEIR PHARMACEUTICAL COMPOSITION AND METHOD FOR ITS RECEIVING | |
| EP0194599A3 (en) | Benzamide derivatives, process for producing the same, and soil fungicides containing the same | |
| RU96101797A (en) | SUBSTITUTED THIOPHENYL SULFONYLMUNE UTIES AND THIOPHENYL SULFONYLTIOMETRICS, METHOD OF THEIR RECEIVING, DRUG AND METHOD | |
| RU2493150C2 (en) | 2,4-pyrimidine diamine compounds and use thereof | |
| KR880701231A (en) | N- (2-substituted alkyl) -N '-((imidazol-4-yl) alkyl) guanidine | |
| SI9600049B (en) | Substituted benzenesulphonyl ureas and thioureas, process for the preparation thereof, use thereof as medicine or as diagnostic as well as medicine containing them | |
| RU94002329A (en) | MODIFIED OLYHODESOXYRIBONUCLEOTIDE, COMPOSITION, TREATMENT METHOD AND INTERMEDIATE CONNECTIONS | |
| KR840005118A (en) | Method for preparing heterocyclic amines | |
| DE59813264D1 (en) | AQUEOUS CATIONIC TENSID PREPARATIONS, A METHOD OF PREPARING THEM AND THEIR USE | |
| RU96102420A (en) | SUBSTITUTED BENZOLSULPHONYLMOLEVANE AND -THYOMOCHARE, METHOD OF THEIR RECEIVING, METHOD OF OBTAINING MEDICINE AND MEDICINE ON THEIR BASIS | |
| KR930021635A (en) | Novel fungicidal triazoles and imidazole derivatives | |
| SI9600040B (en) | Substituted benzensulphonyl ureas and thioureas, process for the preparation thereof and use thereof for the preparation of pharmaceutical preparations as well as pharmaceutical preparations containing them | |
| RU2003107569A (en) | METHOD FOR CONTINUOUS PREPARATION OF CHLORTHIAZOLES USED AS PESTICIDES | |
| RU2219161C2 (en) | Taxane synthesis method | |
| RU96123576A (en) | SUBSTITUTED CHROMANILSULFONIL (THIO) UREA, METHOD FOR PRODUCING THEM AND THEIR APPLICATION, AND ALSO CONTAINING THEIR PHARMACEUTICALS | |
| KR840000481A (en) | Method for preparing herbicidal compound derived from phenoxybenzoic acid | |
| GB1570213A (en) | Imidazoles | |
| SI9600033B (en) | Substituted tiophensulfonyl ureas and thioureas, process for the preparation thereof, use thereof as medicine or as diagnostic as well as medicine containing them | |
| SU493067A3 (en) | The method of obtaining phenylimidazolidinone |