SU493967A3 - Способ получени 2-карбалкоксиаминобензимидазол -5(6)-фенилэфиров - Google Patents
Способ получени 2-карбалкоксиаминобензимидазол -5(6)-фенилэфировInfo
- Publication number
- SU493967A3 SU493967A3 SU1967977A SU1967977A SU493967A3 SU 493967 A3 SU493967 A3 SU 493967A3 SU 1967977 A SU1967977 A SU 1967977A SU 1967977 A SU1967977 A SU 1967977A SU 493967 A3 SU493967 A3 SU 493967A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbalkoxyaminobenzimidazole
- phenylethers
- obtaining
- carbon atoms
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JNQQNFFWBXOYNN-UHFFFAOYSA-N 6-phenylsulfanyl-1h-benzimidazole Chemical compound C=1C=C2N=CNC2=CC=1SC1=CC=CC=C1 JNQQNFFWBXOYNN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- -1 cyanamide carboxylate Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
и повышают температуру до 80°С. После добавлени 200 мл лед ной уксусной кислоты выдерживают реакционную смесь еще 3-4 час при 90°С, затем охлаждают и на ночь помещают в холодильник. Выпавший 5 - фенилмеркаптобензимидазол - 2 - метилкарбаминат отфильтровывают и промывают изопропанолом и водой. После перекристаллизации из диметилформамида получают 82 г чистого 5 - фенилмеркаптобензимидазол-2метилкарбамината с т. пл. 233°С. Предмет изобретени 1. Способ получени 2-карбалкоксиаминобензимидазол-5 (6)-фенилэфиров формулы I NH-COOR R,V где RI - алкил с 1-4 атомами углерода, и Кз - независимо друг от друга атом водорода, гидроксил, алкоксигруппа с 1-4 атомами углерода, галоид, трифторметил, алкил с 1-4 атомами углерода или карбалкоксигруппа с 1-4 атомами углерода, R4 - атом водорода или хлора, X - кислород или сера, отличающийс тем, что производное о-фенилендиамина формулы И R,-A. где JR2, Rs, R4 и X имеют указанные выше значени , конденсируют с цианамидкарбоксилатом формулы III NC-N-COORi(III) где Ri имеет указанное выше значение при рН от 1 до 6, с выделением целевого продукта известными приемами. 2. Способ по п. 1, отличающийс тем, что процесс провод т при температуре от 30 до 100°С.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2164690A DE2164690C3 (de) | 1971-12-27 | 1971-12-27 | Anthelmintisch wirksame 5-Phenoxy- und 5-Phenylthiobenzimidazolyl-(2)-carbamin-säuremethylester und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU493967A3 true SU493967A3 (ru) | 1975-11-28 |
Family
ID=5829297
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1865601A SU492086A3 (ru) | 1971-12-27 | 1972-12-27 | Способ получени 2-карбалкокси-аминобензимидазол-5(6)-фенилэфиров |
| SU1967977A SU493967A3 (ru) | 1971-12-27 | 1973-11-11 | Способ получени 2-карбалкоксиаминобензимидазол -5(6)-фенилэфиров |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1865601A SU492086A3 (ru) | 1971-12-27 | 1972-12-27 | Способ получени 2-карбалкокси-аминобензимидазол-5(6)-фенилэфиров |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US3954791A (ru) |
| JP (1) | JPS5033067B2 (ru) |
| KR (1) | KR780000116B1 (ru) |
| AT (1) | AT320638B (ru) |
| AU (1) | AU465226B2 (ru) |
| BE (1) | BE793358A (ru) |
| BG (2) | BG20591A3 (ru) |
| CA (1) | CA1017750A (ru) |
| CH (2) | CH580080A5 (ru) |
| CS (2) | CS173650B2 (ru) |
| DD (2) | DD110760A5 (ru) |
| DE (1) | DE2164690C3 (ru) |
| DK (1) | DK130293B (ru) |
| EG (1) | EG11122A (ru) |
| ES (1) | ES409860A1 (ru) |
| FI (1) | FI54299C (ru) |
| FR (1) | FR2166048B1 (ru) |
| GB (1) | GB1360180A (ru) |
| HU (1) | HU165060B (ru) |
| IL (1) | IL41170A (ru) |
| IT (1) | IT1043888B (ru) |
| KE (1) | KE2613A (ru) |
| MY (1) | MY7600092A (ru) |
| NL (1) | NL153187B (ru) |
| NO (1) | NO137092C (ru) |
| PL (1) | PL85192B1 (ru) |
| RO (1) | RO71503A (ru) |
| SE (1) | SE395890B (ru) |
| SU (2) | SU492086A3 (ru) |
| ZA (1) | ZA729076B (ru) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965113A (en) * | 1972-12-29 | 1976-06-22 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| HU169503B (ru) * | 1974-02-05 | 1976-12-28 | ||
| RO64921A (fr) * | 1974-05-28 | 1979-07-15 | Syntex Inc | Procede pour la preparation des derives des benzimidazole-2-carbamates |
| DE2432631A1 (de) * | 1974-07-06 | 1976-01-22 | Hoechst Ag | 5-phenylsulfinyl-2-benzimidazol-carbaminsaeureester und verfahren zu ihrer herstellung |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| US4076828A (en) * | 1977-02-17 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles |
| US4076827A (en) * | 1977-04-28 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles |
| US4076825A (en) * | 1977-06-22 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral or topical administration of sulfoxide derivatives of benzimidazoles |
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| YU40704B (en) * | 1977-05-10 | 1986-04-30 | Chinoin Gyogyszer Es Vegyeszet | Process for obtaininga 5(6)-thiobenzamidazole derivatives |
| US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
| US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
| US4154846A (en) * | 1978-06-16 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates |
| EP0028455A1 (en) * | 1979-10-12 | 1981-05-13 | Imperial Chemical Industries Plc | 5-Phenylselenobenzimidazole derivatives, their preparation and anthelmintic or fasciolicidal compositions containing them |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| US4662935A (en) * | 1980-01-14 | 1987-05-05 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| EP0060810B1 (de) * | 1981-03-18 | 1984-10-17 | Ciba-Geigy Ag | Anthelmintika |
| IE56125B1 (en) * | 1982-10-28 | 1991-04-24 | Ici Plc | Indole derivatives |
| WO1990010630A1 (en) * | 1989-03-15 | 1990-09-20 | Janssen Pharmaceutica N.V. | [5(6)-(benzisoxa-, benzisothia- or indazol-3-yl)-1h-benzimidazol-2-yl] carbamates |
| NZ232785A (en) * | 1989-03-15 | 1991-03-26 | Janssen Pharmaceutica Nv | 5-(1,2 benzisoxazol-, benzimidazol and benzisothiazol-3- yl)-1h-benzimadazol-2-yl carbamic acid ester derivatives preparatory processes, intermediates and anthelmintic compositions |
| US5538989A (en) * | 1993-11-10 | 1996-07-23 | Hoechst-Roussel Agri-Vet Company | Fenbendazole formulations |
| US5861142A (en) * | 1996-03-25 | 1999-01-19 | Schick; Mary Pichler | Method for promoting hair, nail, and skin keratinization |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| US7396819B2 (en) | 2003-08-08 | 2008-07-08 | Virbac Corporation | Anthelmintic formulations |
| WO2005094210A2 (en) * | 2004-03-12 | 2005-10-13 | The Hartz Mountain Corporation | Multi-action anthelmintic formulations |
| CA2616512A1 (en) * | 2005-07-28 | 2007-02-08 | Intervet International B.V. | Novel benzimidazole (thio) carbamates with antiparasitic activity and the synthesis thereof |
| US20130197527A1 (en) * | 2006-06-12 | 2013-08-01 | Smith & Nephew, Inc. | Systems, methods and devices for tibial resection |
| KR101403135B1 (ko) | 2006-06-14 | 2014-06-19 | 인터벳 인터내셔널 비.브이. | 벤지미다졸 카르바메이트 및 폴리솔베이트를 포함하는 현탁물 |
| EP3383852A4 (en) * | 2015-11-30 | 2019-08-28 | Children's Medical Center Corporation | COMPOUNDS FOR THE TREATMENT OF PROLIFERATIVE DISEASES |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK131821C (da) * | 1967-03-22 | 1976-03-08 | Smith Kline French Lab | Analogifremgangsmade til fremstilling af en 2-karbalkoksyaminobenzimidazol |
| US3480642A (en) * | 1967-03-22 | 1969-11-25 | Smithkline Corp | Process for producing 2-carbalkoxyaminobenzimidazoles |
| FR2063815A5 (en) * | 1969-10-31 | 1971-07-09 | Aries Robert | Antifungal and anthelmintic benzimidazole carbamates |
-
0
- BE BE793358D patent/BE793358A/xx not_active IP Right Cessation
-
1971
- 1971-12-27 DE DE2164690A patent/DE2164690C3/de not_active Expired
-
1972
- 1972-12-19 RO RO7273205A patent/RO71503A/ro unknown
- 1972-12-20 CS CS5893A patent/CS173650B2/cs unknown
- 1972-12-20 ES ES409860A patent/ES409860A1/es not_active Expired
- 1972-12-20 CH CH1856672A patent/CH580080A5/xx not_active IP Right Cessation
- 1972-12-20 CH CH827476A patent/CH583710A5/xx not_active IP Right Cessation
- 1972-12-20 HU HUHO1535A patent/HU165060B/hu unknown
- 1972-12-20 CS CS8805A patent/CS173615B2/cs unknown
- 1972-12-21 DD DD178527*A patent/DD110760A5/xx unknown
- 1972-12-21 DD DD167796A patent/DD109219A5/xx unknown
- 1972-12-21 FI FI3637/72A patent/FI54299C/fi active
- 1972-12-22 NO NO4753/72A patent/NO137092C/no unknown
- 1972-12-22 NL NL727217532A patent/NL153187B/xx not_active IP Right Cessation
- 1972-12-22 DK DK642872AA patent/DK130293B/da unknown
- 1972-12-22 AT AT1099672A patent/AT320638B/de not_active IP Right Cessation
- 1972-12-22 IT IT33528/72A patent/IT1043888B/it active Protection Beyond IP Right Term
- 1972-12-22 CA CA159,777A patent/CA1017750A/en not_active Expired
- 1972-12-22 AU AU50486/72A patent/AU465226B2/en not_active Expired
- 1972-12-23 BG BG025960A patent/BG20591A3/xx unknown
- 1972-12-23 BG BG22217A patent/BG22080A3/xx unknown
- 1972-12-23 PL PL1972159809A patent/PL85192B1/pl unknown
- 1972-12-25 IL IL41170A patent/IL41170A/en unknown
- 1972-12-26 US US05/318,271 patent/US3954791A/en not_active Expired - Lifetime
- 1972-12-26 KR KR7201961A patent/KR780000116B1/ko not_active Expired
- 1972-12-26 EG EG541/72A patent/EG11122A/xx active
- 1972-12-27 ZA ZA729076A patent/ZA729076B/xx unknown
- 1972-12-27 FR FR7246316A patent/FR2166048B1/fr not_active Expired
- 1972-12-27 SE SE7216998A patent/SE395890B/xx unknown
- 1972-12-27 GB GB5966672A patent/GB1360180A/en not_active Expired
- 1972-12-27 JP JP734324A patent/JPS5033067B2/ja not_active Expired
- 1972-12-27 SU SU1865601A patent/SU492086A3/ru active
-
1973
- 1973-11-11 SU SU1967977A patent/SU493967A3/ru active
-
1976
- 1976-03-22 KE KE2613*UA patent/KE2613A/xx unknown
- 1976-12-30 MY MY92/76A patent/MY7600092A/xx unknown
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