GB1435376A - Benzimidazolyl isothiocyanates methods for their preparation and compositions containing them - Google Patents

Benzimidazolyl isothiocyanates methods for their preparation and compositions containing them

Info

Publication number
GB1435376A
GB1435376A GB2603673A GB2603673A GB1435376A GB 1435376 A GB1435376 A GB 1435376A GB 2603673 A GB2603673 A GB 2603673A GB 2603673 A GB2603673 A GB 2603673A GB 1435376 A GB1435376 A GB 1435376A
Authority
GB
United Kingdom
Prior art keywords
alkyl
benzimidazolyl
halogen
reaction
optionally substituted
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
GB2603673A
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.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1435376A publication Critical patent/GB1435376A/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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—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
    • C07D235/06—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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1435376 Benzimidazolyl - isothiocyanates E R SQUIBB & SONS Inc 31 May 1973 [2 June 1972] 26036/73 Heading C2C Novel compounds I and salts thereof in which R<SP>1</SP> is hydrogen, C 1-7 alkyl optionally substituted by halogen or aryl as defined below, mono- or bi-cyclic aryl optionally substituted by halogen, NO 2 , CF 3 , alkoxy, optionally substituted amido or alkyl as defined above, alkoxycarbonyl, aryloxycarbonyl, dialkylaminoalkyl, acyl or carbamoyl or a 2-thiazolin-2-yl or 5,6 - dihydro - 4H - 1,3 - thiazin - 2 - yl radical optionally substituted by C 1-7 alkyl, halogen, di-C 1-7 alkylamino-alkyl or aryl as defined above. R<SP>2</SP> is a saturated or unsaturated N, S or O containing heterocycle having 6 members and 1 and 2 hetero-atoms and optionally substituted by C 1-7 alkyl, halogen or di-C 1-7 alkylaminoalkyl and R<SP>3</SP> is hydrogen, C 1-7 alkyl, halogen or C 1-7 alkoxy are prepared by reaction of a corresponding amino-benzimidazole (II) with a thiocarbamic derivative Hal-CS-Y where Hal is chlorine or bromine and Y is chlorine, bromine or dialkylamino (preferably thiophosgene). Compounds I (R<SP>1</SP> = H, Bu, B 3 , EtOCO, Et-NH-CO-, B 3 O-CO-, B 3 -CO, Me 2 N- (CH 2 ) 2 -, 5,6 - dihydro - 4H - 1,3 - thiazin - 2- yl, 2 - thiazolin - 2 - yl or 5 - phenyl - 2 - thiazolin-2-yl, R<SP>2</SP> = pyridyl, pyrimidyl, pyrazinyl, 2-methyl-pyridyl or 2-ethyl-pyridyl, R<SP>3</SP> = H, Br, Pr or PrO) are prepared. Amino benzoxazole derivatives (II) are prepared by reduction of the corresponding nitro derivative. The nitro benzimidazoles of Formula V in which R 1 is hydrogen are prepared by (1) reaction of an R<SP>3</SP> and nitro substituted o-phenylenediamine with an acid chloride R<SP>2</SP>-CO-Cl to form an amide which undergoes intermolecular condensation or (2) reaction of an R<SP>3</SP> and nitro substituted o-phenylenediamine with an aldehyde R<SP>2</SP>-CHO to form a Schiffs base which is cyclized by intermolecular condensation. Replacement of hydrogen by a substituent R<SP>1</SP> in the benzimidazole is carried out by (1) reaction with a halide R<SP>1'</SP>-X in which X is chlorine or bromine and R<SP>1'</SP> is R<SP>1</SP> other than hydrogen or the specified thiazoline or thiazine group or (2) formation of a metal salt of the nitrobenzimidazole (V) by reaction with a metal hydride and reaction with a haloalkylisothiocyanate S = C = N-A-X where A is a chain of 2 or 3 carbon atoms optionally substituted by C 1-7 alkyl, halogen, di-C 1-7 alkylaminoalkyl or aryl. 2 - (2 - Thienyl) - 5 - benzimidazolyl, 2 - (2- furyl) - 5 - benzimidazolyl, 1 - (2 - thiazolin - 2- yl) - 2 - methyl - 5 (and 6) - benzimidazolyl and 1 - (2 - dimethylaminoethyl) - 2 - (2 - furyl) - 5- (and 6)-benzimidazolyl esters of isothiocyanic acid are also prepared as illustrations of the above methods. Compounds I are anthelmintic agents and disinfectants and form with a carrier or diluent a pharmaceutical composition or animal feed.
GB2603673A 1972-06-02 1973-05-31 Benzimidazolyl isothiocyanates methods for their preparation and compositions containing them Expired GB1435376A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US25905872A 1972-06-02 1972-06-02

Publications (1)

Publication Number Publication Date
GB1435376A true GB1435376A (en) 1976-05-12

Family

ID=22983326

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2603673A Expired GB1435376A (en) 1972-06-02 1973-05-31 Benzimidazolyl isothiocyanates methods for their preparation and compositions containing them

Country Status (7)

Country Link
JP (1) JPS4961317A (en)
AU (1) AU477230B2 (en)
CA (1) CA1029382A (en)
DE (1) DE2328095A1 (en)
FR (1) FR2186267B1 (en)
GB (1) GB1435376A (en)
NL (1) NL7307668A (en)

Also Published As

Publication number Publication date
AU5637673A (en) 1974-12-05
AU477230B2 (en) 1976-10-21
NL7307668A (en) 1973-12-04
FR2186267A1 (en) 1974-01-11
CA1029382A (en) 1978-04-11
DE2328095A1 (en) 1973-12-13
FR2186267B1 (en) 1976-12-31
JPS4961317A (en) 1974-06-14

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee