DE2334631A1 - 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung - Google Patents
5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellungInfo
- Publication number
- DE2334631A1 DE2334631A1 DE19732334631 DE2334631A DE2334631A1 DE 2334631 A1 DE2334631 A1 DE 2334631A1 DE 19732334631 DE19732334631 DE 19732334631 DE 2334631 A DE2334631 A DE 2334631A DE 2334631 A1 DE2334631 A1 DE 2334631A1
- Authority
- DE
- Germany
- Prior art keywords
- carbamic acid
- formula
- phenylsulfinyl
- acid
- manufacture
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 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 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- -1 also permanganates Chemical class 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-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
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241001547406 Hyostrongylus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 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 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000507 anthelmentic effect Effects 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
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940126601 medicinal product Drugs 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
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 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)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334631 DE2334631A1 (de) | 1973-07-07 | 1973-07-07 | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
| GB2879374A GB1428933A (en) | 1973-07-07 | 1974-06-28 | 5-phenyl-sulphinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
| NL7408945A NL7408945A (nl) | 1973-07-07 | 1974-07-02 | Werkwijze voor het bereiden van 5-fenylsulfi- nyl-2-benzimidazoolcarbaminezuur. |
| CS744656A CS218553B2 (en) | 1973-07-07 | 1974-07-02 | Method of making the alkylesters of the substituted 5-phenylsulfinyl-2-benzimidazolcarbam acid |
| ES427869A ES427869A1 (es) | 1973-07-07 | 1974-07-02 | Procedimiento para la preparacion de esteres alcoholicos deacido 5-fenilsulfinil-2-bencimidazol-carbamico. |
| CH911374A CH605821A5 (en, 2012) | 1973-07-07 | 1974-07-03 | |
| IL45189A IL45189A (en) | 1973-07-07 | 1974-07-03 | 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
| CA203,893A CA1030970A (en) | 1973-07-07 | 1974-07-03 | 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
| FI2052/74A FI60202C (fi) | 1973-07-07 | 1974-07-04 | Foerfarande foer framstaellning av nya saosom maskmedel verksamma 5-fenylsulfinyl-2-bensimidazolkarbaminsyraalkylestrar |
| DD179700A DD114262A5 (en, 2012) | 1973-07-07 | 1974-07-04 | |
| AU70899/74A AU489525B2 (en) | 1973-07-07 | 1974-07-05 | 5-phenylsulfinyl-2-benzimidazoyl-carbamic acid esters and process for their manufacture |
| IT24889/74A IT1050720B (it) | 1973-07-07 | 1974-07-05 | Esteri dell acido 5 menilsolfinil 2 benzimidazolil carbammico e processo per la loro preparazione |
| ZA00744335A ZA744335B (en) | 1973-07-07 | 1974-07-05 | 5-phenylsulfinyl-2-benzimidazolylcarbamic acid esters and process for their manufacture |
| FR7423523A FR2235688B1 (en, 2012) | 1973-07-07 | 1974-07-05 | |
| AT555674A AT337201B (de) | 1973-07-07 | 1974-07-05 | Verfahren zur herstellung von neuen 5-phenylsulfinylbenzimidazolyl-2-carbaminsaurealkylestern |
| DK362674A DK362674A (en, 2012) | 1973-07-07 | 1974-07-05 | |
| SE7408868A SE7408868L (en, 2012) | 1973-07-07 | 1974-07-05 | |
| NO742457A NO141758C (no) | 1973-07-07 | 1974-07-05 | Analogifremgangsmaate til fremstilling av anthelmintisk virksomme 5-fenylsulfinyl-2-benzimidazolkarbaminsyreestere |
| EG259/74A EG11414A (en) | 1973-07-07 | 1974-07-06 | 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
| JP49076915A JPS5840547B2 (ja) | 1973-07-07 | 1974-07-06 | ５− フエニルスルフイニル −２− ベンズイミダゾ−ル − カルバミンサンエステルノセイホウ |
| BE146318A BE817364A (fr) | 1973-07-07 | 1974-07-08 | (5-phenylsulfinyl-2-benzimidazolyl)-carbamates |
| AT863276A AT349826B (de) | 1973-07-07 | 1976-11-19 | Verfahren zur bekaempfung von helminthen |
| HK81/80A HK8180A (en) | 1973-07-07 | 1980-03-06 | 5-phenylsulphinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
| MY272/80A MY8000272A (en) | 1973-07-07 | 1980-12-30 | 5-phenylsulphinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334631 DE2334631A1 (de) | 1973-07-07 | 1973-07-07 | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2334631A1 true DE2334631A1 (de) | 1975-03-27 |
Family
ID=5886239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732334631 Ceased DE2334631A1 (de) | 1973-07-07 | 1973-07-07 | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792610A (en) * | 1987-06-13 | 1988-12-20 | Hoechst Aktiengesellschaft | Process for the preparation of 5-phenylsulfinyl-1H-2-(methoxycarbonylamino)-benzimidazole |
Families Citing this family (3)
| 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 |
| 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 |
Citations (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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
Non-Patent Citations (2)
| Title |
|---|
| EHRHART G. u. RUSCHIG H.: Arzneimittel, 2.Aufl., Bd.5, Chemotherapeutica Teil 2, Verlag Chemie Weinheim, 1972, S.28-39 * |
| In Betracht gezogene ältere Patente: DE-PS 23 66 070 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792610A (en) * | 1987-06-13 | 1988-12-20 | Hoechst Aktiengesellschaft | Process for the preparation of 5-phenylsulfinyl-1H-2-(methoxycarbonylamino)-benzimidazole |
| EP0295327A3 (de) * | 1987-06-13 | 1990-03-14 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von 5-Phenylsulfinyl-1H-1-(methoxycarbonylamino)-benzimidazol |
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 |
| 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 |
| FI60202C (fi) | 1981-12-10 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |