GB1087345A - 2-(chloro-2'-furyl)benzimidazoles - Google Patents
2-(chloro-2'-furyl)benzimidazolesInfo
- Publication number
- GB1087345A GB1087345A GB48788/64A GB4878864A GB1087345A GB 1087345 A GB1087345 A GB 1087345A GB 48788/64 A GB48788/64 A GB 48788/64A GB 4878864 A GB4878864 A GB 4878864A GB 1087345 A GB1087345 A GB 1087345A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- chloro
- prepared
- compound
- formula
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel benzimidazoles of the formula <FORM:1087345/C2/1> wherein R1 represents a hydrogen atom or a C1- 5 alkyl, aralkyl or acyl radical, one of R5 and R6 represent a hydrogen or halogen atom or a C1- 5 alkyl, C1- 5 alkoxy, C1- 5 alkylthio, phenoxy, phenylthio, phenyl or halophenyl radical and the other represents hydrogen and n is 1 or 2, are prepared by reacting a substituted aniline and a substituted furan of the respective formulae <FORM:1087345/C2/2> wherein A represents hydrogen or a nitro group and B represents a carboxy, esterified carboxy or haloformyl radical, to form an amide of the formula <FORM:1087345/C2/3> when A is hydrogen, nitrating this amide to convert A to nitro, and reducing the nitro compound with hydrogen (under certain conditions and when n is 2, the reduction may cause the elimination of one chlorine atom); by reacting the required o-phenylene diamine with the required chloro-substituted-2-furfural, the process being effected in the presence of nitrobenzene benzene or being followed by reaction with an oxidizing agent on the intermediate Schiff type base formed; or by reacting an amidine of the formula <FORM:1087345/C2/4> wherein R5, R6 and n have the above significance (obtainable from the required aniline and required chloro substituted 2-cyano-furan), with a chlorinating or brominating agent to produce the corresponding N-haloamidine and treating this compound with a base. Ethyl - 2,3,4,5 - tetrachloro - tetrahydrofuran - 2 - carboxylate is prepared by treating ethyl 2-furoate with chlorine, is converted into a mixture of ethyl mono- and poly-chloro-2-furoates by heating the mixture may be separated by fractionally distilling, saponifying the fraction boiling between 123 DEG and 145 DEG C. at 20 mm. pressure, forming the calcium salts of the resulting mixture of acids, filtering off the precipitated calcium salts and acidifying the filtrate to precipitate 3,5-dichloro-2-furoic acid or treating an aqueous solution of the said calcium salts with hydrochloric acid and extracting 4,5-dichloro-2-furoic acid. 4 - Chloro - 2 - furoic acid is prepared by the zinc dust-HCl treatment of the corresponding 4,5-dichloro-compound. 4 - Fluoro - 41 - aminobiphenyl is prepared by nitrating 4-fluoro-biphenyl and reducing the resulting 4-fluoro-41-nitrobiphenyl. Pharmaceutical compositions having anthelmintic activity contain as the active ingredient a compound of the first formula above. The compositions may be in the form of capsules, tablets, boluses, drenches or solutions.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33493263A | 1963-12-31 | 1963-12-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1087345A true GB1087345A (en) | 1967-10-18 |
Family
ID=23309502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB48788/64A Expired GB1087345A (en) | 1963-12-31 | 1964-12-01 | 2-(chloro-2'-furyl)benzimidazoles |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE657726A (en) |
BR (1) | BR6465547D0 (en) |
CH (2) | CH467285A (en) |
DK (3) | DK115848B (en) |
FR (2) | FR1461360A (en) |
GB (1) | GB1087345A (en) |
NL (1) | NL6414806A (en) |
SE (1) | SE316482B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09502432A (en) * | 1993-09-10 | 1997-03-11 | チバ−ガイギー アクチエンゲゼルシャフト | PHOTOCHROMIC COMPOUND, PROCESS FOR PRODUCING THE SAME, INTERMEDIATE PRODUCT FOR THE PRODUCTION, AND USE THEREOF |
-
1964
- 1964-12-01 GB GB48788/64A patent/GB1087345A/en not_active Expired
- 1964-12-18 NL NL6414806A patent/NL6414806A/xx unknown
- 1964-12-22 BR BR16554764A patent/BR6465547D0/en unknown
- 1964-12-29 BE BE657726D patent/BE657726A/xx unknown
- 1964-12-30 CH CH1680464A patent/CH467285A/en unknown
- 1964-12-30 CH CH1766868A patent/CH474536A/en not_active IP Right Cessation
- 1964-12-30 DK DK645164A patent/DK115848B/en unknown
- 1964-12-30 FR FR489A patent/FR1461360A/en not_active Expired
- 1964-12-30 SE SE1588364A patent/SE316482B/xx unknown
-
1965
- 1965-03-29 FR FR11111A patent/FR4341M/fr not_active Expired
-
1966
- 1966-05-27 DK DK274166A patent/DK112171B/en unknown
- 1966-05-27 DK DK274266A patent/DK115701B/en unknown
Also Published As
Publication number | Publication date |
---|---|
SE316482B (en) | 1969-10-27 |
CH467285A (en) | 1969-01-15 |
DK112171B (en) | 1968-11-18 |
FR4341M (en) | 1966-08-08 |
BR6465547D0 (en) | 1973-08-09 |
CH474536A (en) | 1969-06-30 |
FR1461360A (en) | 1966-12-09 |
DK115701B (en) | 1969-11-03 |
DK115848B (en) | 1969-11-17 |
NL6414806A (en) | 1965-07-02 |
BE657726A (en) | 1965-06-29 |
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