GB1365515A - 6-tetrahydro imidazol/2 1-b/thiazoles - Google Patents

6-tetrahydro imidazol/2 1-b/thiazoles

Info

Publication number
GB1365515A
GB1365515A GB4131471A GB4131471A GB1365515A GB 1365515 A GB1365515 A GB 1365515A GB 4131471 A GB4131471 A GB 4131471A GB 4131471 A GB4131471 A GB 4131471A GB 1365515 A GB1365515 A GB 1365515A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
phenyl
treating
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
GB4131471A
Inventor
L D Spicer
J J Hand
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
Priority to GB4131471A priority Critical patent/GB1365515A/en
Priority to CY93372A priority patent/CY933A/en
Publication of GB1365515A publication Critical patent/GB1365515A/en
Priority to MY7600073A priority patent/MY7600073A/en
Priority to KE279177A priority patent/KE2791A/en
Priority to HK61877A priority patent/HK61877A/en
Priority to MY7800129A priority patent/MY7800129A/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

Landscapes

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

Abstract

1365515 6-(Substituted phenyl)-5,6-dihydro or 2,3,5,6 - tetrahydro - imidazo - thiazoles AMERICAN CYANAMID CO 3 Sept 1971 41314/71 Heading C2C Novel DL and L isomers of compounds of Formula (I) and salts thereof where R 1 and R 2 are hydrogen, C 1-10 alkyl, C 2-8 alkenyl, C 3-7 cycloalkyl, hydroxy C 1-4 alkyl, C 1-4 alkanoyl oxy-C 1-4 alkyl, C 1-4 alkoxy C 1-4 alkyl, benzyl, substituted benzyl, phenyl ethyl, substituted phenyl ethyl, mono- and dinitro phenyl, 2- and 4-pyridyl, 2- and 4- pyrimidinyl, 2-thiazolylpyridylmethyl, furfuryl, tetrahydrofurfuryl or R 5 CO wherein R 5 is hydrogen, C 1-9 alkyl C 2-7 alkenyl, C 3-7 cycloalkyl, C 1-6 haloalkyl C 1-6 aminoalkyl, mono- and di- C 1-4 alkyl-amino C 1-4 alkyl, piperidino- C 1-4 alkyl, pyrrolidino C 1-4 alkyl, morpholino C 1-4 alkyl, C 1-4 alkoxy C 1-4 alkyl, phenyl, substituted phenyl furyl, tetrahydrofuryl, naphthyl, C 1-8 alkoxyamino, mono- or di-C 1-4 alkylamino, piperidino, pyrrolidino or morpholino, or NR 1 R 2 taken together represents piperidino, pyrrolidino, morpholino or the group (C 1-4 alkyl) 2 -NCH = N- and R 3 and R 4 are selected from hydrogen, halogen or nitro; the term substituted refers to mono-, di- or trisubstitution by halogen, nitro or C 1-4 alkoxy, = is a single or double bond and when R 3 and R 4 are hydrogen only one of R 1 and R 2 may be hydrogen, are prepared (1) by reaction of a compound IV in which R 6 is hydrogen or C 1-4 alkanoyl and X is an anion with (a) concentrated sulphuric acid and treating the compound formed with an alkali metal hydroxide or ammonium hydroxide or (b) thionyl chloride at 40-75‹ C. and treating the reaction product with acetic anhydride at 50-140‹ C., removing excess C 1-4 alkanoyl anhydride, treating the reaction product with strong mineral acid and treating the acid solution with an alkali metal hydroxide or ammonium hydroxide, (2) by reaction of a compound of Formula II where R 1 is hydrogen or C 1-10 alkyl, and R 3 and R 4 are hydrogen, halogen or nitro, with an acid chloride or anhydride (R 2 COCl or (R 2 CO) 2 O) where R 2 is C 1-4 alkyl, C 3-7 cycloalkyl phenyl or C 1-4 alkoxy or (3) from substituted acetophenones of general Formula III using procedures described in U.S.A. Specification 3,673,205. Compounds of general Formula I may also be prepared by alkylation of amino group using the corresponding iodoalkyl or by nitration or bromination in the phenyl ring. The nitro group may also be reduced to the amino group. Compounds of general Formula I are useful in treating helminthiasis in warm-blooded animals and may be administered orally or parenterally.
GB4131471A 1971-09-03 1971-09-03 6-tetrahydro imidazol/2 1-b/thiazoles Expired GB1365515A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB4131471A GB1365515A (en) 1971-09-03 1971-09-03 6-tetrahydro imidazol/2 1-b/thiazoles
CY93372A CY933A (en) 1971-09-03 1972-09-03 6-(aminophenyl)-5,6-dihydro-or 2,3,5,6-tetra-hydroimidazol (2,1-b) thiazoles
MY7600073A MY7600073A (en) 1971-09-03 1976-12-30 6-(aminophenyl)-5,6-dihydro-or 2,3,5,6-tetra-hydrolmidazo[2,1-b]thiazoles
KE279177A KE2791A (en) 1971-09-03 1977-11-07 6-(aminophenyl)-5,6-dihydro- or 2,3,5,6-tetra-hydroimidazo (2,1-b) thiazoles
HK61877A HK61877A (en) 1971-09-03 1977-12-15 6-(aminophenyl)-5,6-dihydro- or 2,3,5,6-tetrahydroimidazo (2,1-b) thiazoles
MY7800129A MY7800129A (en) 1971-09-03 1978-12-30 6-(aminophenyl)-5,6-dihydro-or 2,3,5-6-tetra-hyydroimidazo [2,1-b]thiazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4131471A GB1365515A (en) 1971-09-03 1971-09-03 6-tetrahydro imidazol/2 1-b/thiazoles

Publications (1)

Publication Number Publication Date
GB1365515A true GB1365515A (en) 1974-09-04

Family

ID=10419124

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4131471A Expired GB1365515A (en) 1971-09-03 1971-09-03 6-tetrahydro imidazol/2 1-b/thiazoles

Country Status (5)

Country Link
CY (1) CY933A (en)
GB (1) GB1365515A (en)
HK (1) HK61877A (en)
KE (1) KE2791A (en)
MY (2) MY7600073A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4112102A (en) * 1976-05-01 1978-09-05 Pfizer Inc. Halopyridyl derivatives of m-aminotetramisole as anthelmintics
EP0076622A1 (en) * 1981-10-07 1983-04-13 Beecham Group Plc Anthelmintics
US4389406A (en) 1980-05-30 1983-06-21 Beecham Group Limited Meta-pyrazolylaminotetramisole analogs and their use in pharmaceutical compositions
WO2006079642A1 (en) * 2005-01-28 2006-08-03 Janssen Pharmaceutica N.V. Anthelmintic imidazol-thiazole derivates

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4112102A (en) * 1976-05-01 1978-09-05 Pfizer Inc. Halopyridyl derivatives of m-aminotetramisole as anthelmintics
US4389406A (en) 1980-05-30 1983-06-21 Beecham Group Limited Meta-pyrazolylaminotetramisole analogs and their use in pharmaceutical compositions
EP0076622A1 (en) * 1981-10-07 1983-04-13 Beecham Group Plc Anthelmintics
WO2006079642A1 (en) * 2005-01-28 2006-08-03 Janssen Pharmaceutica N.V. Anthelmintic imidazol-thiazole derivates
EA011024B1 (en) * 2005-01-28 2008-12-30 Янссен Фармацевтика Н.В. Anthelmintic imidazol-thiazole derivatives

Also Published As

Publication number Publication date
MY7600073A (en) 1976-12-31
HK61877A (en) 1977-12-23
MY7800129A (en) 1978-12-31
CY933A (en) 1978-06-23
KE2791A (en) 1977-12-09

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years