IL45189A - 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture - Google Patents
5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufactureInfo
- Publication number
- IL45189A IL45189A IL45189A IL4518974A IL45189A IL 45189 A IL45189 A IL 45189A IL 45189 A IL45189 A IL 45189A IL 4518974 A IL4518974 A IL 4518974A IL 45189 A IL45189 A IL 45189A
- Authority
- IL
- Israel
- Prior art keywords
- benzimidazolyl
- carbamic acid
- phenylsulfinyl
- ester
- phenylthio
- Prior art date
Links
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
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- 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)
Description
The present invention relates to 5-phenylsulfinyl-2-benz- iaiidazolyl-earbamle aeld esters and to a process for their manufacture.
Benzimldazolyl carbamic aeld alkyl esters carrying alkyl or acyl groups in 5(6) position are known to be anthelmintic agents (P.Actor et al, Nature 213. 321 (1 67 ) I DOS 2.029.637 ) .
Object of this invention are 5-phenyleulfinyl-2-.benziinida- zolyl-carbamic acid alkyl esters of the formula (l) H in which R stands for alkyl of 1 to carbon atoms, in particular methyl* ethyl» propyl( isoporpyl* butyl* sec- butyl* tert.-butyl* preferably methyl and ethyl* R1 stands for hydrogen* alkyl of 1 to % carbon atoms, chlorine where ned bromine* or methoxy* and R2 stands for hydrogen* methyl 3.7.74 chlorine or bromine* Farther object of this Invention is a process for the manufacture of 5-phenyleulfinyl-2-benzimidazolyl earbamie acid alkyl esters of formula (l) » in which R is defined as above, which comprises oxidizing a phenylthio compound of the formula (2) in which R,R and R are defined as above by means of an oxidizing agent* As oxidizing agents* there are used preferably equivalent amounts of hydro- eroxide in an organic acid· preferably glacial acetic acid* per-acids, such as peracetic acid* pertri luoro- acetic acid or metachloroperbenzoic acid, as well as nit ic^ acid or chromic acid in glacial acetic acid, or the salts oi~ these acids; moreover, permanganates, hypochlorites, per^-chlorates, periodates and nitrogen oxides.
The reaction may advantageously be carried out by adding 30 % hydrogen peroxide to a suspension of the phenylthio compound of the formula (2) in glacial acetic acid, and stirring this mixture at room temperature until a clear solution has formed. The reaction may, however, also be carried out at an elevated temperature of up to about 70°C. The sulfoxide formed is separated by adding water to the reaction solution. The separated precipitate is isolated by filtration.
The corresponding phenylthio derivative used as darting material is obtained by reacting 5-phenylthio-o-phenylene diamine with S-methylthio-urea and an alkyl-chloroformiate Israel Patent Specification No. 41170. according to GeiTOan--G-ffeniegt¾g&e^h^^ The 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid alkyl esters of the invention are valuable chemotherapeutic agents and are suitable for combating diseases caused by parasites in mammals . hTmrams--ajttd--anima-ls. They are particularly active against a great number of helminths, for example Haemonchus, Trichostrongylus, Ostertagia, Strongyloides, Cooperia, Chabertia, Oesophagostomum, Hyostrongylus, Ankylostoma, Askaris and Heterakis. Particularly marked is the activity against gastro-intestinal Strongylides, which are above all infesting ruminants. The infestation of animals by these parasites causes great economical damage, so that the compounds of the invention are mainly used in veterinary drugs .
The active substances of formula 1 are administered in doses of from 0.5 to 50 mg per kg of body weight for 1 to 14 days, depending on the individual case. ^ For oral administration, there may be used tablets, dragees, capsules, powder, granules or pastes which contain the active substances in conjunction with the usual excipients and adjuvants, such as starch, cellulose powder, talcum, magnesium stearate, sugar, gelatin, calcium carbonate, finely divided silicic acid, carboxy-methyl cellulose or similar substances.
For parenteral administration, there may be used solutions, for example oily solutions prepared using sesame oil, castor oil or synthetic triglycerides, optionally with the addition of surface-active substances, such as sorbitane fatty acid ester. In addition, there may be used aqueous suspensions prepared with the use of ethoxylated sorbitane fatty acid esters, optionally with the addition of thickeners, such as polyethylene glycol or carboxymethyl cellulose.
The concentrations of the active substances of the invention in the preparations prepared therewith are preferably in the range of from 2 to 20 % by weight for veterinary drugs; for the use as medicaments for humans, the concentrations of the active substances are preferably in the range of from 20 to 80 % by weight.
The following Examples illustrate the invention.
E X A M P L E ; 5-Phenylsulfinyl-2-benzimidazolyl-carbamic acid methyl ester A mixture of 75 g of 5-phenylthio-2-benzimidazolyl-carbamic acid methyl ester, 750 ml of glacial acetic acid and 250 ml of 30 % hydrogen peroxide was stirred at room temperature until a clear solution had formed, which took about 2 hours.
Subsequently, 1.5 1 of water were added, the solution was heated to 80°C for a short time and the precipitate was sucmon-filtered when cool. After washing and drying, 65 g of 5-phenyl-sulfinyl-2-benzimidazolyl-carbaraic acid methyl ester were obtained, melting point: 248°C (with decomposition).
In an analogous manner, there were prepared; 2. From 5~phenylthio-2~benzimidazolyl~carbamic acid ethyl ester, the 5-phenylsulfinyl-2~benzimidazolyl-carbamic acid ethyl ester, m.p. 230°C (decomposition); 3. from 5~phenylthio-2-benzimidazolyl-carbamic acid isopropyl ester, the 5-phenylsulfinyl~2-benzimidazolyl-carbamic acid isopropyl ester, m.p. 237°C (decomposition); 4. from 5~phenylthio~2-benzimidazolyl-carbamic acid birtyl ester, the 5-phenylsulfinyl~2-benzimidazolyl-carbamic acid butyl ester, m.p. 225°C (decomposition); 5. from 5-(3-methyl-phenylthio)~2-benzimidazolyl-carbamic acid methyl ester, the 5-(3-methyl-phenylsulfinyl)-2-benzimida- zolyl-carbamic acid methyl ester, m.p. 284°C (decomposition); 6. from 5-(4-methyl~phen3'lthio)-2-benzimidazolyl-carbamic acid methyl ester, the 5-(4-methyl-phenylsulfinyl)-2-benz- imidazolyl-carbamic acid methyl ester, m.p. 285°C (decomposition); 7. from 5-(4-chloro-phenylthio)-2-benzimidazolyl-carbamic acid methyl ester, the 5-(4-chloro-phenylsulfinyl)-2-benzimida- zolyl-carbamic acid methyl ester, m.p. 287°C (decomposition); . from 5-(4-chloro-phenylth o)-2-benzimidazolyl-carbamic acid isopropyl ester, the 5-(4-chloro-phenylsulfinyl)~2-benz- imidazolyl-carbamic acid isopropyl ester, m.p. 301 °C (decomposition); 9. from 5-(4-methoxy-phenylthio)-2-benzimidazolyl-carbamic acid methyl ester, the 5-(4-methoxy-phenylsulfinyl)-2- ™ benzimidazoljl-carbamic acid methyl este ; m.p. 275°C (decomposition) ; 10. from 5-(4-methoxy-phenylthio)~2~benzimidazolyl-carbamic acid isopropyl ester, the 5-(4~methoxy-phenylsulfinyl)- 2-benzimidazolyl-carbamic acid isopropyl ester, m.p. 227°C (decomposition); 11. from 5-(2,5-'-dichloro-phenylthio)-2-benzimidazolyl-carbamic acid methyl ester, the 5-(2,5-dichloro~phenyisulfinyl)- 2-benzimidazolyl-carbamic acid methyl ester, m.p. 285°C (decomposition) ; 12. from 5-(2 ,5-dichloro-phenylthio)-2-benzimidazolyl-carbamic acid isopropyl ester, the 5-(2i 5-dichloro-phenylsulfinyl)- 2-benzimidazolyl-carbamic acid isopropyl ester, m.p. 265°C (decomposition); 13· from 5-(2-methyl-5-tert.-butyl-phenylthio )-2-benzimidazolyl- carbamic acid methyl ester, the 5-(2-methyl-5-tert.-butyl- phenylsulfinyl)-2-benzimidazolyl-carbamic acid methyl ester, m.p. 2j56°C (decomposition); 1 . from 5-(2-methyl-5-tert.-butyl-phenylthio )-2-benzimidazolyl- carbamic acid isopropyl ester, the 5-(2-methyl-5-tert.- butyl-phenylsulfinyl)-2-benzimida∑olyl-c'arbamic acid isopropyl ester, m.p. 241 °C (decomposition) and 15. from 5- (4-tert.-butyl-phenylthio)-2-benzimidazolyl-carbamic acid methyl ester, the 5-( -tert.-butyl-phenylsulfinyl)-2~ benzimidazolyl-carbamic acid methyl ester, m.p. 240°C (decomposition).
Claims (1)
1. WHAT IS CLAIMED A add ester of the formula which R stands for an alkyl group of 1 to 4 carbon atoms R staids for hydrogen alkyl of 1 to 4 ne or and R stands for methyl chlorine or A process for the manufacture of a c add alkyl ester of the formula spec fied 1n claim 1 which comprises oxidizing a th1o der1vat1 of the formula n which R2 are as 1n claim by of an oxidizing An anthelmint ic composition conta1n1r g as active idlent an effective quantity of a compound claimed n claim A method for combating helminths 1n excludinc humans effective quantity of a compound cla ned 1n claim insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334631 DE2334631A1 (en) | 1973-07-07 | 1973-07-07 | 5-PHENYLSULFINYL-2-BENZIMIDAZOLE CARBAMIC ACID ESTERS AND THE METHOD FOR THEIR MANUFACTURE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45189A0 IL45189A0 (en) | 1974-10-22 |
| IL45189A true IL45189A (en) | 1977-03-31 |
Family
ID=5886239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45189A IL45189A (en) | 1973-07-07 | 1974-07-03 | 5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5840547B2 (en) |
| AT (1) | AT337201B (en) |
| BE (1) | BE817364A (en) |
| CA (1) | CA1030970A (en) |
| CH (1) | CH605821A5 (en) |
| CS (1) | CS218553B2 (en) |
| DD (1) | DD114262A5 (en) |
| DE (1) | DE2334631A1 (en) |
| DK (1) | DK362674A (en) |
| EG (1) | EG11414A (en) |
| ES (1) | ES427869A1 (en) |
| FI (1) | FI60202C (en) |
| FR (1) | FR2235688B1 (en) |
| GB (1) | GB1428933A (en) |
| HK (1) | HK8180A (en) |
| IL (1) | IL45189A (en) |
| IT (1) | IT1050720B (en) |
| MY (1) | MY8000272A (en) |
| NL (1) | NL7408945A (en) |
| NO (1) | NO141758C (en) |
| SE (1) | SE7408868L (en) |
| ZA (1) | ZA744335B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1107749B (en) * | 1977-10-06 | 1985-11-25 | Montedison Spa | BENZIMIDAZOLCARBAMMATE PARTICULARLY ACTIVE AGAINST GASTROENTERIC AND PULMONARY PARASITES |
| DK157547C (en) * | 1978-12-06 | 1990-06-25 | Montedison Spa | METHOD OF ANALOGUE FOR THE PREPARATION OF 5 (6) SUBSTITUTED BENZIMIDAZOLE CARBAMATES. |
| DE3719783A1 (en) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | METHOD FOR PRODUCING 5-PHENYLSULFINYL-1H-2- (METHOXYCARBONYLAMINO) - BENZIMIDAZOLE |
| CN102863392A (en) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | Method for greatly reducing amount of solvent usage in production process of oxfendazole |
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/en not_active Ceased
-
1974
- 1974-06-28 GB GB2879374A patent/GB1428933A/en not_active Expired
- 1974-07-02 NL NL7408945A patent/NL7408945A/en not_active Application Discontinuation
- 1974-07-02 CS CS744656A patent/CS218553B2/en unknown
- 1974-07-02 ES ES427869A patent/ES427869A1/en not_active Expired
- 1974-07-03 CA CA203,893A patent/CA1030970A/en 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
- 1974-07-04 DD DD179700A patent/DD114262A5/xx unknown
- 1974-07-04 FI FI2052/74A patent/FI60202C/en active
- 1974-07-05 AT AT555674A patent/AT337201B/en not_active IP Right Cessation
- 1974-07-05 SE SE7408868A patent/SE7408868L/xx not_active Application Discontinuation
- 1974-07-05 IT IT24889/74A patent/IT1050720B/en active
- 1974-07-05 DK DK362674A patent/DK362674A/da unknown
- 1974-07-05 ZA ZA00744335A patent/ZA744335B/en unknown
- 1974-07-05 NO NO742457A patent/NO141758C/en unknown
- 1974-07-05 FR FR7423523A patent/FR2235688B1/fr not_active Expired
- 1974-07-06 JP JP49076915A patent/JPS5840547B2/en not_active Expired
- 1974-07-06 EG EG259/74A patent/EG11414A/en active
- 1974-07-08 BE BE146318A patent/BE817364A/en not_active IP Right Cessation
-
1980
- 1980-03-06 HK HK81/80A patent/HK8180A/en unknown
- 1980-12-30 MY MY272/80A patent/MY8000272A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7408868L (en) | 1975-01-08 |
| ES427869A1 (en) | 1976-12-16 |
| NO742457L (en) | 1975-02-03 |
| CA1030970A (en) | 1978-05-09 |
| CH605821A5 (en) | 1978-10-13 |
| NL7408945A (en) | 1975-01-09 |
| AT337201B (en) | 1977-06-27 |
| AU7089974A (en) | 1976-01-08 |
| FR2235688B1 (en) | 1978-07-28 |
| JPS5040567A (en) | 1975-04-14 |
| BE817364A (en) | 1975-01-08 |
| ZA744335B (en) | 1975-07-30 |
| EG11414A (en) | 1977-02-28 |
| CS218553B2 (en) | 1983-02-25 |
| JPS5840547B2 (en) | 1983-09-06 |
| MY8000272A (en) | 1980-12-31 |
| DK362674A (en) | 1975-03-17 |
| DD114262A5 (en) | 1975-07-20 |
| IL45189A0 (en) | 1974-10-22 |
| HK8180A (en) | 1980-03-14 |
| FI60202C (en) | 1981-12-10 |
| FI60202B (en) | 1981-08-31 |
| NO141758B (en) | 1980-01-28 |
| IT1050720B (en) | 1981-03-20 |
| FR2235688A1 (en) | 1975-01-31 |
| FI205274A (en) | 1975-01-08 |
| NO141758C (en) | 1980-05-07 |
| GB1428933A (en) | 1976-03-24 |
| ATA555674A (en) | 1976-10-15 |
| DE2334631A1 (en) | 1975-03-27 |
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