FI60202C - Foerfarande foer framstaellning av nya saosom maskmedel verksamma 5-fenylsulfinyl-2-bensimidazolkarbaminsyraalkylestrar - Google Patents
Foerfarande foer framstaellning av nya saosom maskmedel verksamma 5-fenylsulfinyl-2-bensimidazolkarbaminsyraalkylestrar Download PDFInfo
- Publication number
- FI60202C FI60202C FI2052/74A FI205274A FI60202C FI 60202 C FI60202 C FI 60202C FI 2052/74 A FI2052/74 A FI 2052/74A FI 205274 A FI205274 A FI 205274A FI 60202 C FI60202 C FI 60202C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- benzimidazolylcarbamic
- verksamma
- nya
- maskmedel
- Prior art date
Links
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 230000000507 anthelmentic effect Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- -1 phenylthio compound Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 3
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 description 3
- GUVHJRKHTWAPJG-UHFFFAOYSA-N [6-(benzenesulfinyl)-1h-benzimidazol-2-yl]carbamic acid Chemical compound C=1C=C2NC(NC(=O)O)=NC2=CC=1S(=O)C1=CC=CC=C1 GUVHJRKHTWAPJG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- HDDSHPAODJUKPD-UHFFFAOYSA-N fenbendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 HDDSHPAODJUKPD-UHFFFAOYSA-N 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960004454 oxfendazole Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 241001126259 Nippostrongylus brasiliensis Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960005473 fenbendazole Drugs 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 229950007337 parbendazole Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- YLEPPBFOGUYOEI-UHFFFAOYSA-N 4-phenylsulfanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1SC1=CC=CC=C1 YLEPPBFOGUYOEI-UHFFFAOYSA-N 0.000 description 1
- 241000760149 Aspiculuris Species 0.000 description 1
- 241000760148 Aspiculuris tetraptera Species 0.000 description 1
- JUHGTMVVRGYLPU-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)S(=O)C2=CC3=C(C=C2)N=C(N3)NC(=O)O Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)S(=O)C2=CC3=C(C=C2)N=C(N3)NC(=O)O JUHGTMVVRGYLPU-UHFFFAOYSA-N 0.000 description 1
- SODDYWWIYANVBM-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)SC2=CC3=C(C=C2)N=C(N3)NC(=O)OC SODDYWWIYANVBM-UHFFFAOYSA-N 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241001547406 Hyostrongylus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
- 229960003439 mebendazole Drugs 0.000 description 1
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- QLKGNHAAQMXCKL-UHFFFAOYSA-N methyl N-[6-(3-methylphenyl)sulfanyl-1H-benzimidazol-2-yl]carbamate Chemical compound COC(NC=1NC2=C(N1)C=CC(=C2)SC2=CC(=CC=C2)C)=O QLKGNHAAQMXCKL-UHFFFAOYSA-N 0.000 description 1
- ZFAYUNVSPNUTQP-UHFFFAOYSA-N methyl N-[6-(3-methylphenyl)sulfinyl-1H-benzimidazol-2-yl]carbamate Chemical compound CC=1C=C(C=CC1)S(=O)C1=CC2=C(N=C(N2)NC(=O)OC)C=C1 ZFAYUNVSPNUTQP-UHFFFAOYSA-N 0.000 description 1
- VHLBXYZKINRKNO-UHFFFAOYSA-N methyl N-[6-(4-methylphenyl)sulfanyl-1H-benzimidazol-2-yl]carbamate Chemical compound COC(NC=1NC2=C(N1)C=CC(=C2)SC2=CC=C(C=C2)C)=O VHLBXYZKINRKNO-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 238000005406 washing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2334631 | 1973-07-07 | ||
| DE19732334631 DE2334631A1 (de) | 1973-07-07 | 1973-07-07 | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI205274A7 FI205274A7 (en, 2012) | 1975-01-08 |
| FI60202B FI60202B (fi) | 1981-08-31 |
| FI60202C true FI60202C (fi) | 1981-12-10 |
Family
ID=5886239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2052/74A FI60202C (fi) | 1973-07-07 | 1974-07-04 | Foerfarande foer framstaellning av nya saosom maskmedel verksamma 5-fenylsulfinyl-2-bensimidazolkarbaminsyraalkylestrar |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5840547B2 (en, 2012) |
| AT (1) | AT337201B (en, 2012) |
| BE (1) | BE817364A (en, 2012) |
| CA (1) | CA1030970A (en, 2012) |
| CH (1) | CH605821A5 (en, 2012) |
| CS (1) | CS218553B2 (en, 2012) |
| DD (1) | DD114262A5 (en, 2012) |
| DE (1) | DE2334631A1 (en, 2012) |
| DK (1) | DK362674A (en, 2012) |
| EG (1) | EG11414A (en, 2012) |
| ES (1) | ES427869A1 (en, 2012) |
| FI (1) | FI60202C (en, 2012) |
| FR (1) | FR2235688B1 (en, 2012) |
| GB (1) | GB1428933A (en, 2012) |
| HK (1) | HK8180A (en, 2012) |
| IL (1) | IL45189A (en, 2012) |
| IT (1) | IT1050720B (en, 2012) |
| MY (1) | MY8000272A (en, 2012) |
| NL (1) | NL7408945A (en, 2012) |
| NO (1) | NO141758C (en, 2012) |
| SE (1) | SE7408868L (en, 2012) |
| ZA (1) | ZA744335B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1107749B (it) * | 1977-10-06 | 1985-11-25 | Montedison Spa | Benzimidazolcarbammato particolarmente attivo contro i parassiti gastroenterici e polmonari |
| DD147539A5 (de) * | 1978-12-06 | 1981-04-08 | Montedison Spa | Herstellung von in 5(6)-stellung substituierten benzimidazol-carbamaten |
| DE3719783A1 (de) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung von 5-phenylsulfinyl-1h-2-(methoxycarbonylamino)- benzimidazol |
| CN102863392A (zh) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | 一种奥芬达唑生产过程中大幅减少溶剂使用量的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
-
1973
- 1973-07-07 DE DE19732334631 patent/DE2334631A1/de not_active Ceased
-
1974
- 1974-06-28 GB GB2879374A patent/GB1428933A/en not_active Expired
- 1974-07-02 NL NL7408945A patent/NL7408945A/xx not_active Application Discontinuation
- 1974-07-02 CS CS744656A patent/CS218553B2/cs unknown
- 1974-07-02 ES ES427869A patent/ES427869A1/es not_active Expired
- 1974-07-03 IL IL45189A patent/IL45189A/en unknown
- 1974-07-03 CH CH911374A patent/CH605821A5/xx not_active IP Right Cessation
- 1974-07-03 CA CA203,893A patent/CA1030970A/en not_active Expired
- 1974-07-04 DD DD179700A patent/DD114262A5/xx unknown
- 1974-07-04 FI FI2052/74A patent/FI60202C/fi active
- 1974-07-05 AT AT555674A patent/AT337201B/de not_active IP Right Cessation
- 1974-07-05 IT IT24889/74A patent/IT1050720B/it active
- 1974-07-05 NO NO742457A patent/NO141758C/no unknown
- 1974-07-05 FR FR7423523A patent/FR2235688B1/fr not_active Expired
- 1974-07-05 SE SE7408868A patent/SE7408868L/xx not_active Application Discontinuation
- 1974-07-05 ZA ZA00744335A patent/ZA744335B/xx unknown
- 1974-07-05 DK DK362674A patent/DK362674A/da unknown
- 1974-07-06 JP JP49076915A patent/JPS5840547B2/ja not_active Expired
- 1974-07-06 EG EG259/74A patent/EG11414A/xx active
- 1974-07-08 BE BE146318A patent/BE817364A/xx not_active IP Right Cessation
-
1980
- 1980-03-06 HK HK81/80A patent/HK8180A/xx unknown
- 1980-12-30 MY MY272/80A patent/MY8000272A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS218553B2 (en) | 1983-02-25 |
| ZA744335B (en) | 1975-07-30 |
| JPS5040567A (en, 2012) | 1975-04-14 |
| IL45189A (en) | 1977-03-31 |
| FI60202B (fi) | 1981-08-31 |
| NO742457L (en, 2012) | 1975-02-03 |
| NL7408945A (nl) | 1975-01-09 |
| EG11414A (en) | 1977-02-28 |
| IL45189A0 (en) | 1974-10-22 |
| SE7408868L (en, 2012) | 1975-01-08 |
| NO141758C (no) | 1980-05-07 |
| DE2334631A1 (de) | 1975-03-27 |
| DD114262A5 (en, 2012) | 1975-07-20 |
| FR2235688A1 (en, 2012) | 1975-01-31 |
| GB1428933A (en) | 1976-03-24 |
| HK8180A (en) | 1980-03-14 |
| AU7089974A (en) | 1976-01-08 |
| FR2235688B1 (en, 2012) | 1978-07-28 |
| IT1050720B (it) | 1981-03-20 |
| ES427869A1 (es) | 1976-12-16 |
| BE817364A (fr) | 1975-01-08 |
| FI205274A7 (en, 2012) | 1975-01-08 |
| CH605821A5 (en, 2012) | 1978-10-13 |
| JPS5840547B2 (ja) | 1983-09-06 |
| CA1030970A (en) | 1978-05-09 |
| ATA555674A (de) | 1976-10-15 |
| MY8000272A (en) | 1980-12-31 |
| AT337201B (de) | 1977-06-27 |
| DK362674A (en, 2012) | 1975-03-17 |
| NO141758B (no) | 1980-01-28 |
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