GB1286603A - 2-substituted polyhalobenzimidazoles - Google Patents

2-substituted polyhalobenzimidazoles

Info

Publication number
GB1286603A
GB1286603A GB44896/70A GB4489670A GB1286603A GB 1286603 A GB1286603 A GB 1286603A GB 44896/70 A GB44896/70 A GB 44896/70A GB 4489670 A GB4489670 A GB 4489670A GB 1286603 A GB1286603 A GB 1286603A
Authority
GB
United Kingdom
Prior art keywords
reacting
alkyl
halo
csnh
tri
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
Application number
GB44896/70A
Inventor
Michael Herbert Fisher
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1286603A publication Critical patent/GB1286603A/en
Expired legal-status Critical Current

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
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen atoms
    • 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
    • C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
    • 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
    • C07D235/26—Oxygen atoms
    • 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
    • C07D235/28—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1286603 Benzimidazoles MERCK & CO Inc 21 Sept 1970 [26 Sept 1969] 44896/70 Heading C2C The invention comprises compounds of formula and their salts with alkali or alkaline earth metals, and with pharmaceutically acceptable amines and acids, wherein R is CN, CSNH 2 , CSNH alkyl, CSN(alkyl) 2 , S-alkyl, SO 2 alkyl or 2-thiazolin-2-yl ; R 1 , R 2 , R 3 , R 4 are each F, Cl, Br or I, or one of them may be H; and R 5 is H, alkyl, alkoxyalkyl, C 2-6 alkenyl, carboxyalkyl, carboalkoxyalkyl, C 1-6 alkanoyl, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl, and when R is CN, R 5 may also be OH, alkoxy, carboxyalkoxy, carboalkoxyalkoxy, sulphoalkoxy or amino-C 2-6 -alkoxy (possibly N-alkyl or N,N- dialkyl substituted). In examples, these compounds are prepared by (1) (R=CN : Ia) dehydrating with SOCl 2 the tri- or tetra-halo- 2-formylbenzimidazole oxime, reacting the tri- or terra-halo-2-chlorobenzimidazole with NaCN, or reacting the tri- or tetra-halo-2-trichloromethylbenimidozole (II) with NH 3 ; (2) (R=CSNH 2 ) reacting Ia with H 2 S; (3) (R=CSNHMe or CSNEt 2 ) reacting ethyl trichlorobenzimidazolyl-2- formimidate with H 2 S followed by MeNH 2 or Et 2 NH; (4) (R = 2-thiazolin-2-yl) reacting II with 2-aminoethanethiol; (5) (R = SMe and SO 2 Me) reacting trichlorobenzimidazole-2-thiol with MeI/NaOH, and oxidizing the product with a peracid; (6) replacing the 1-H atom by reaction with an alkanoic acid anhydride, or the 1-H atom or the H of a 1-OH group by reaction with a halo-substituted compound; (7) (R 5 = NH 2 CH 2 CH 2 O) reacting a 2 - cyano - 1 - phthalimidoethoxytrihalobemimidazole with N 2 H 4 ; (8) removing a 1 -methoxymethyl group with pyridine hydrochloride; (9) standard interconversion reactions of functional groups in a sidechain in the 1-position; (10) salt formation. Intermediates otherwise prepared are:-2- methyl- and 2-styryl-4,6,7-trichlorobenzimidazoles and their 1-hydroxy derivatives; and 4,5,7 -trichlorobenzimidazolone. Veterinary compositions having anthelmintic and anticoccidial activity (which may be administered in conventional forms), and pesticidal compositions having herbicidal and bactericidal activity, comprise compounds of the above formula.
GB44896/70A 1969-09-26 1970-09-21 2-substituted polyhalobenzimidazoles Expired GB1286603A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US86145269A 1969-09-26 1969-09-26

Publications (1)

Publication Number Publication Date
GB1286603A true GB1286603A (en) 1972-08-23

Family

ID=25335828

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44896/70A Expired GB1286603A (en) 1969-09-26 1970-09-21 2-substituted polyhalobenzimidazoles

Country Status (9)

Country Link
JP (1) JPS4932535B1 (en)
CA (1) CA950468A (en)
CH (1) CH556341A (en)
DE (1) DE2047369A1 (en)
FR (1) FR2070090B1 (en)
GB (1) GB1286603A (en)
IL (1) IL35291A0 (en)
NL (1) NL7013343A (en)
ZA (1) ZA706553B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0219192A2 (en) * 1985-08-08 1987-04-22 Schering Agrochemicals Limited Fungicides
US5482956A (en) * 1992-11-06 1996-01-09 Bayer Aktiengesellschaft Method of treating parastic protozoa with substituted benzimidazoles
WO2011058139A1 (en) * 2009-11-12 2011-05-19 Selvita Sp. Z O. O. A compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent
US8604217B2 (en) 2009-11-12 2013-12-10 Selvita S.A. Compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50137570A (en) * 1974-04-18 1975-10-31
JPS5139426U (en) * 1974-09-18 1976-03-24
JPS5175327A (en) * 1974-12-25 1976-06-29 Fujitsu Ltd
LU75684A1 (en) * 1976-08-27 1978-04-13
IL54474A (en) * 1977-04-12 1982-04-30 Ciba Geigy Ag Benzimidazole derivatives,their preparation and anthelmintic compositions containing them
FR2521141A1 (en) * 1982-02-09 1983-08-12 Rhone Poulenc Agrochimie NOVEL DERIVATIVES OF CYANO-2 BENZIMIDAZOLE, THEIR PREPARATION AND THEIR USE AS FUNGICIDES
FR2601010A1 (en) * 1986-07-02 1988-01-08 Rhone Poulenc Agrochimie Sulphonylbenzimidazole derivatives, their preparation and their use as fungicides
FR2607811A1 (en) * 1986-12-05 1988-06-10 Rhone Poulenc Agrochimie Sulphonylbenzimidazole derivatives, their preparation and their use as fungicides
DE4237567A1 (en) * 1992-11-06 1994-05-11 Bayer Ag Pesticides
DE4242183A1 (en) * 1992-12-15 1994-06-16 Bayer Ag Use of CN-substituted benzimidazoles
DE4416116A1 (en) * 1994-05-06 1995-11-09 Bayer Ag Substituted benzimidazoles
DE19920551A1 (en) 1999-05-05 2000-11-09 Bayer Ag Substituted benzimidazoles, their preparation and their use as agents against parasitic protozoa
DE10131149A1 (en) * 2001-06-28 2003-01-16 Bayer Ag Substituted gasoline midazoles for combating endoparasites
DE102009038950A1 (en) 2009-08-26 2011-03-03 Bayer Animal Health Gmbh New antiparasitic combination of drugs

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1567111A1 (en) * 1965-08-06 1970-04-16 Shell Int Research Herbicides
US3480643A (en) * 1967-05-09 1969-11-25 American Cyanamid Co Alkylsulfonylbenzimidazoles

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0219192A2 (en) * 1985-08-08 1987-04-22 Schering Agrochemicals Limited Fungicides
EP0219192A3 (en) * 1985-08-08 1987-06-24 Schering Agrochemicals Limited Fungicides
US5482956A (en) * 1992-11-06 1996-01-09 Bayer Aktiengesellschaft Method of treating parastic protozoa with substituted benzimidazoles
AU670317B2 (en) * 1992-11-06 1996-07-11 Bayer Animal Health Gmbh Use of substituted benzimidazoles
WO2011058139A1 (en) * 2009-11-12 2011-05-19 Selvita Sp. Z O. O. A compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent
CN102712601A (en) * 2009-11-12 2012-10-03 赛尔维他股份公司 A compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent
US8604217B2 (en) 2009-11-12 2013-12-10 Selvita S.A. Compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent

Also Published As

Publication number Publication date
NL7013343A (en) 1971-03-30
IL35291A0 (en) 1970-11-30
FR2070090A1 (en) 1971-09-10
DE2047369A1 (en) 1971-04-01
ZA706553B (en) 1972-05-31
CA950468A (en) 1974-07-02
JPS4932535B1 (en) 1974-08-31
CH556341A (en) 1974-11-29
FR2070090B1 (en) 1974-09-20

Similar Documents

Publication Publication Date Title
GB1286603A (en) 2-substituted polyhalobenzimidazoles
US3238101A (en) Blood vessel constricting compositions and methods of using same
PT72878A (en) Process for preparing mannich-base hydroxamic acid prodrugs for the improved delivery of non-steroidal anti-inflammatory agents
JPS62161728A (en) Antibacterial
GB1328321A (en) 2-heteroaryl benzimidazole derivatives useful as anthelmintics
MY102919A (en) Pleuromutilin derivatives process for their preparation and their use.
GB1307205A (en) Isoindoline derivatives
PL84493B1 (en)
GB966796A (en) Compositions containing substituted benzimidazoles
GB830832A (en) New quinolones and therapeutic compositions containing them
DD287495A5 (en) METHOD FOR PRODUCING HERTEROZYCLIC NITROGEN COMPOUNDS
GB1476333A (en) Urea and hydantoin derivatives and plant-growth regulating compositions
JPS55100380A (en) 11imidazoll22ylidenee33heterocyclic urea derivative*its manufacture and pharmaceutic composition having antidepressive activity
ES341316A1 (en) Salicylanilide Derivatives, their preparation and Compositions containing them
DE3804346A1 (en) tert-Butylphenylpyridyl amides, process for their preparation, and medicaments containing these compounds
GB1353545A (en) S-triazine derivatives and their salts and process for producing them
GB1173312A (en) Heterocyclic Compounds
PL92078B1 (en)
GB1026401A (en) Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them
GB1092654A (en) Process for the production of new iminocarbonic ester derivatives
US3792052A (en) Hydrazinecarbodithioate derivatives and metal chelates thereof
CH648025A5 (en) CHINOXALINE-1,4-DIOXYD DERIVATIVES.
GB1415528A (en) 2-thiocarbonylamino acetamidocephalosporanic acid compounds
US3962454A (en) Bis-(1-alkyl-5-nitro-imidazolyl-2-alkyl)-compounds
US3207754A (en) Heterocyclic sulphonamido compounds

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee