GB2011896A - Anthelmintic carbamic acid ester derivatives of benzimidazoles - Google Patents
Anthelmintic carbamic acid ester derivatives of benzimidazolesInfo
- Publication number
- GB2011896A GB2011896A GB7849940A GB7849940A GB2011896A GB 2011896 A GB2011896 A GB 2011896A GB 7849940 A GB7849940 A GB 7849940A GB 7849940 A GB7849940 A GB 7849940A GB 2011896 A GB2011896 A GB 2011896A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- benzimidazoles
- anthelmintic
- image
- acid ester
- 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.)
- Withdrawn
Links
- 230000000507 anthelmentic effect Effects 0.000 title abstract 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Plural Heterocyclic Compounds (AREA)
Abstract
Benzimidazoles are provided having the structure <IMAGE> wherein R is lower alkyl or phenyl- lower alkyl and A is <IMAGE> wherein R1 is lower alkyl, R2 is hydrogen or lower alkyl, or R1 and R2 may be taken together with the carbons to which they are attached to form a cycloalkenyl ring, R3 is hydrogen or lower alkyl, and y is 0 or 1; <IMAGE> wherein R4 and R5 are the same or different and are hydrogen or lower alkyl, R6 is lower alkyl or phenyl, and R7 and R8 are the same or different and are chlorine, bromine, fluorine or iodine, m is 0 to 3, n is 0 to 3, and m+n is </=5; or <IMAGE> wherein R9, R10 and R11 may be the same or different and may be lower alkyl or lower alkoxy, z is 0, 1 or 2 and p is 1 to 5, with the proviso that when A is <IMAGE> R is lower alkyl. These compounds have anthelmintic properties.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/868,148 US4156006A (en) | 1978-01-09 | 1978-01-09 | Vinyl sulfide derivatives of benzimidazoles |
| US05/870,391 US4136174A (en) | 1978-01-18 | 1978-01-18 | Benzimidazolecarbamates and method |
| US05/885,717 US4138493A (en) | 1978-03-13 | 1978-03-13 | 2,2-Dihalo-1(3)-lower alkyl-cyclopropylalkylthio benzimidazole derivatives, compositions thereof and method of use in treating tapeworms and whipworms |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2011896A true GB2011896A (en) | 1979-07-18 |
Family
ID=27420450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7849940A Withdrawn GB2011896A (en) | 1978-01-09 | 1978-12-22 | Anthelmintic carbamic acid ester derivatives of benzimidazoles |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54100374A (en) |
| AU (1) | AU4185678A (en) |
| CA (1) | CA1117538A (en) |
| DE (1) | DE2856796A1 (en) |
| FR (1) | FR2422645A1 (en) |
| GB (1) | GB2011896A (en) |
| IE (1) | IE47530B1 (en) |
| IT (1) | IT1102784B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK157547C (en) * | 1978-12-06 | 1990-06-25 | Montedison Spa | METHOD OF ANALOGUE FOR THE PREPARATION OF 5 (6) SUBSTITUTED BENZIMIDAZOLE CARBAMATES. |
-
1978
- 1978-11-23 AU AU41856/78A patent/AU4185678A/en active Pending
- 1978-11-27 CA CA000316928A patent/CA1117538A/en not_active Expired
- 1978-12-06 IE IE2412/78A patent/IE47530B1/en unknown
- 1978-12-22 GB GB7849940A patent/GB2011896A/en not_active Withdrawn
- 1978-12-26 JP JP16452778A patent/JPS54100374A/en active Pending
- 1978-12-28 IT IT31383/78A patent/IT1102784B/en active
- 1978-12-28 FR FR7836791A patent/FR2422645A1/en not_active Withdrawn
- 1978-12-29 DE DE19782856796 patent/DE2856796A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU4185678A (en) | 1979-07-19 |
| FR2422645A1 (en) | 1979-11-09 |
| DE2856796A1 (en) | 1979-07-12 |
| CA1117538A (en) | 1982-02-02 |
| IE47530B1 (en) | 1984-04-18 |
| IE782412L (en) | 1979-07-09 |
| JPS54100374A (en) | 1979-08-08 |
| IT1102784B (en) | 1985-10-07 |
| IT7831383A0 (en) | 1978-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |