GB1320179A - 7-acyl-6-aryl-6,7-dihydro-5h-imidazo 2,1,b thiazolium salts - Google Patents

7-acyl-6-aryl-6,7-dihydro-5h-imidazo 2,1,b thiazolium salts

Info

Publication number
GB1320179A
GB1320179A GB5630070A GB5630070A GB1320179A GB 1320179 A GB1320179 A GB 1320179A GB 5630070 A GB5630070 A GB 5630070A GB 5630070 A GB5630070 A GB 5630070A GB 1320179 A GB1320179 A GB 1320179A
Authority
GB
United Kingdom
Prior art keywords
general formula
dihydro
thiazolin
ylidene
imidazo
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
GB5630070A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1320179A publication Critical patent/GB1320179A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1320179 6 - Phenyl - 7 - acyl - 6,7 - dihydro- 5H - imidazo[2,1 - b]thiazolium salts AMERICAN CYANAMID CO 26 Nov 1970 [15 Dec 1969] 56300/70 Heading C2C Novel 6 - phenyl - 7 - acyl - 6,7 - dihydro- 5H-imidazo[2,1-b]thiazolium salts of the general formula wherein R 1 is a hydrogen atom or a C 1-17 alkyl, C 1-6 haloalkyl, C 1-4 alkoxy, C 2-5 carboalkoxy- C 1-4 alkyl, phenyl, halophenyl or C 1-4 alkylphenyl, R 2 is a hydrogen or halogen atom or a nitro, trifluoromethyl or C 1-5 alkanoylamino group and X<SP>(-)</SP> is a chloride, bromide or perchlorate ion, and optically active isomers thereof are prepared (a) when X is a chlorine or bromine atom, by treatment of an N-[3-phenethyl-4-thiazolin-2-ylidene]-amide salt of the general formula with an anhydride in an inert organic solvent at 50-200‹ C., by heating of the said salt until it melts, or by neutralization of the said salt with a basic ion exchange resin or a trialkylamine, and heating of the free base obtained in an inert solvent; (b) when X is a chlorine or bromine atom, by reaction of a 5,6-dihydro-6- phenylimidazo[2,1-b]thiazole of the general formula (in the form of a racemic mixture or optically active isomers) with an acid halide or anhydride of the respective general formulae R 1 COY, wherein Y is a chlorine or bromine atom, and (R 1 CO) 2 O in an inert solvent, using at least an equimolar amount of the said halide or anhydride; and (c) when X- is a perchlorate ion, by treatment of an aqueous solution of the corresponding chloride or bromide with sodium perchlorate. N - [3 - Phenethyl - 4 - thiazolin - 2 - ylidene]- amide salts of the second general formula above are prepared by reaction of an N-[3-(#-hydroxyphenethyl)-4-thiazolin-2-ylidene].amide of the general formula with thionyl chloride, phosphorus trichloride or phosphorus tribromide. N - [3 - (# - Hydroxy - phenethyl) - 4 - thiazolin- 2-ylidene]-amides of the sixth general formula above are prepared (a) by treatment of the corresponding 2-imino-3-(#-hydroxyphenethyl)- thiazoline with at least one molar equivalent of an anhydride of the fifth general formula above in an inert solvent or (b) by borohydride reduction of an N-(3-phenacyl-4-thiazolin-2-ylidene)- amide of the general formula Pharmaceutical compositions having anthelmintic activity comprise, as active ingredient, a 6 - phenyl - 7 - acyl - 6,7 - dihydro - 5H - imidazo[2,1-b]thiazolium salt of the first general formula above, together with a pharmaceutically acceptable carrier or diluent, and may be administered orally or parenterally.
GB5630070A 1969-12-15 1970-11-26 7-acyl-6-aryl-6,7-dihydro-5h-imidazo 2,1,b thiazolium salts Expired GB1320179A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BR215163/69A BR6915163D0 (en) 1969-12-15 1969-12-15 CHEMICAL PROCESS

Publications (1)

Publication Number Publication Date
GB1320179A true GB1320179A (en) 1973-06-13

Family

ID=4081664

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5630070A Expired GB1320179A (en) 1969-12-15 1970-11-26 7-acyl-6-aryl-6,7-dihydro-5h-imidazo 2,1,b thiazolium salts

Country Status (11)

Country Link
AU (1) AU2264370A (en)
BE (1) BE760217A (en)
BR (1) BR6915163D0 (en)
DE (1) DE2061770A1 (en)
ES (1) ES386482A1 (en)
FR (1) FR2081358B1 (en)
GB (1) GB1320179A (en)
IL (1) IL35740A0 (en)
IT (1) IT1047909B (en)
NL (1) NL7017760A (en)
ZA (1) ZA707849B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1445669A1 (en) * 1964-03-26 1969-03-13 Akad Wissenschaften Ddr Process for the preparation of 2,3,5,6-tetrahydro-imidazo [2,1-b] thiazolium salts substituted in the 7-position
NL131034C (en) * 1964-05-11

Also Published As

Publication number Publication date
AU2264370A (en) 1972-06-01
BE760217A (en) 1971-06-11
ZA707849B (en) 1971-08-25
IT1047909B (en) 1980-10-20
ES386482A1 (en) 1973-11-16
IL35740A0 (en) 1971-01-28
FR2081358A1 (en) 1971-12-03
NL7017760A (en) 1971-06-17
FR2081358B1 (en) 1974-06-21
DE2061770A1 (en) 1971-07-01
BR6915163D0 (en) 1973-05-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees