SU492086A3 - Способ получени 2-карбалкокси-аминобензимидазол-5(6)-фенилэфиров - Google Patents
Способ получени 2-карбалкокси-аминобензимидазол-5(6)-фенилэфировInfo
- Publication number
- SU492086A3 SU492086A3 SU1865601A SU1865601A SU492086A3 SU 492086 A3 SU492086 A3 SU 492086A3 SU 1865601 A SU1865601 A SU 1865601A SU 1865601 A SU1865601 A SU 1865601A SU 492086 A3 SU492086 A3 SU 492086A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- nitro
- amino
- chloro
- methylcarbamate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004987 o-phenylenediamines Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- -1 5- (3 - chlorophenoxy) - benzimidazole Chemical compound 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 2
- KCPDTSRPPDALMQ-UHFFFAOYSA-N 6-phenoxy-1h-benzimidazole Chemical compound C=1C=C2N=CNC2=CC=1OC1=CC=CC=C1 KCPDTSRPPDALMQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- FJVIHKKXPLPDSV-UHFFFAOYSA-N 4-phenoxybenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=CC=C1 FJVIHKKXPLPDSV-UHFFFAOYSA-N 0.000 description 1
- 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
- NFOLEKQSKIQPKQ-UHFFFAOYSA-N CC1=CC=C(OC2=CC3=C(N=CN3)C=C2)C=C1 Chemical compound CC1=CC=C(OC2=CC3=C(N=CN3)C=C2)C=C1 NFOLEKQSKIQPKQ-UHFFFAOYSA-N 0.000 description 1
- CVHQHBTZJJLPAB-UHFFFAOYSA-M C[S+]=C(N)N.[O-]S(O)(=O)=O Chemical compound C[S+]=C(N)N.[O-]S(O)(=O)=O CVHQHBTZJJLPAB-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RPZBLCPBVGRZSW-UHFFFAOYSA-N OC1=CC=CC=C1OC1=CC=C(N=CN2)C2=C1 Chemical compound OC1=CC=CC=C1OC1=CC=C(N=CN2)C2=C1 RPZBLCPBVGRZSW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- SSBRSHIQIANGKS-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;hydrogen sulfate Chemical compound NC(N)=O.OS(O)(=O)=O SSBRSHIQIANGKS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960004001 benznidazole Drugs 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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)
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 |
|---|---|
| SU492086A3 true SU492086A3 (ru) | 1975-11-15 |
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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1967977A SU493967A3 (ru) | 1971-12-27 | 1973-11-11 | Способ получени 2-карбалкоксиаминобензимидазол -5(6)-фенилэфиров |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US3954791A (en, 2012) |
| JP (1) | JPS5033067B2 (en, 2012) |
| KR (1) | KR780000116B1 (en, 2012) |
| AT (1) | AT320638B (en, 2012) |
| AU (1) | AU465226B2 (en, 2012) |
| BE (1) | BE793358A (en, 2012) |
| BG (2) | BG22080A3 (en, 2012) |
| CA (1) | CA1017750A (en, 2012) |
| CH (2) | CH580080A5 (en, 2012) |
| CS (2) | CS173650B2 (en, 2012) |
| DD (2) | DD109219A5 (en, 2012) |
| DE (1) | DE2164690C3 (en, 2012) |
| DK (1) | DK130293B (en, 2012) |
| EG (1) | EG11122A (en, 2012) |
| ES (1) | ES409860A1 (en, 2012) |
| FI (1) | FI54299C (en, 2012) |
| FR (1) | FR2166048B1 (en, 2012) |
| GB (1) | GB1360180A (en, 2012) |
| HU (1) | HU165060B (en, 2012) |
| IL (1) | IL41170A (en, 2012) |
| IT (1) | IT1043888B (en, 2012) |
| KE (1) | KE2613A (en, 2012) |
| MY (1) | MY7600092A (en, 2012) |
| NL (1) | NL153187B (en, 2012) |
| NO (1) | NO137092C (en, 2012) |
| PL (1) | PL85192B1 (en, 2012) |
| RO (1) | RO71503A (en, 2012) |
| SE (1) | SE395890B (en, 2012) |
| SU (2) | SU492086A3 (en, 2012) |
| ZA (1) | ZA729076B (en, 2012) |
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 (en, 2012) * | 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 |
| SE443977B (sv) * | 1977-05-10 | 1986-03-17 | Chinoin Gyogyszer Es Vegyeszet | Forfarande for framstellning av 5(6)-tio-bensimidazolderivat |
| US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
| US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
| 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 |
| ZA837829B (en) * | 1982-10-28 | 1984-08-29 | 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 |
| US7582612B2 (en) * | 2004-03-12 | 2009-09-01 | Hartz Mountain Corporation | Multi-action anthelmintic formulations |
| DK1913009T3 (da) * | 2005-07-28 | 2010-08-16 | Intervet Int Bv | Nye benzimidazol(thio)carbamater med antiparasitisk virkning samt syntese heraf |
| CN102283698B (zh) * | 2006-06-12 | 2016-02-24 | 史密夫和内修有限公司 | 用于进行胫骨切除的引导装置 |
| AR061351A1 (es) | 2006-06-14 | 2008-08-20 | Intervet Int Bv | Composicion de carbamato de bencimidazol |
| CA3043549C (en) | 2015-11-30 | 2023-11-21 | Children's Medical Center Corporation | Compounds for treating proliferative diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480642A (en) * | 1967-03-22 | 1969-11-25 | Smithkline Corp | Process for producing 2-carbalkoxyaminobenzimidazoles |
| DK131821C (da) * | 1967-03-22 | 1976-03-08 | Smith Kline French Lab | Analogifremgangsmade til fremstilling af en 2-karbalkoksyaminobenzimidazol |
| 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 CH CH1856672A patent/CH580080A5/xx not_active IP Right Cessation
- 1972-12-20 CS CS5893A patent/CS173650B2/cs unknown
- 1972-12-20 CH CH827476A patent/CH583710A5/xx not_active IP Right Cessation
- 1972-12-20 ES ES409860A patent/ES409860A1/es not_active Expired
- 1972-12-20 CS CS8805A patent/CS173615B2/cs unknown
- 1972-12-20 HU HUHO1535A patent/HU165060B/hu unknown
- 1972-12-21 DD DD167796A patent/DD109219A5/xx unknown
- 1972-12-21 FI FI3637/72A patent/FI54299C/fi active
- 1972-12-21 DD DD178527*A patent/DD110760A5/xx unknown
- 1972-12-22 CA CA159,777A patent/CA1017750A/en not_active Expired
- 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 NO NO4753/72A patent/NO137092C/no unknown
- 1972-12-22 AU AU50486/72A patent/AU465226B2/en not_active Expired
- 1972-12-22 NL NL727217532A patent/NL153187B/xx not_active IP Right Cessation
- 1972-12-22 DK DK642872AA patent/DK130293B/da unknown
- 1972-12-23 BG BG22217A patent/BG22080A3/xx unknown
- 1972-12-23 PL PL1972159809A patent/PL85192B1/pl unknown
- 1972-12-23 BG BG025960A patent/BG20591A3/xx 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 EG EG541/72A patent/EG11122A/xx active
- 1972-12-26 KR KR7201961A patent/KR780000116B1/ko not_active Expired
- 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 SU SU1865601A patent/SU492086A3/ru active
- 1972-12-27 JP JP734324A patent/JPS5033067B2/ja not_active Expired
-
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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