Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-01-19
2000-08-22
Lambkin, Deborah C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 76, 549 79, C07D33312, C07D33322, C07D33324
Patent
active
061074950
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new thienylcyclohexane derivatives, processes for their preparation and their use as new industrial products for the synthesis of thienylcyclohexyl derivatives, and more particularly cyclic (thienyl-cyclohexyl) amines.
A subject of the invention is the compounds of general formula I ##STR1## in racemic form, or in the form of substantially pure diastereoisomers or enantiomers, in which radical of formula OR.sub.1 or NR.sub.2 R.sub.3 in which R.sub.1, R.sub.2 and R.sub.3 represent, independently, a hydrogen atom or an alkyl, alkenyl or alkynyl group, or more identical or different substituents chosen from halogen atoms; the substituents hydroxy; alkoxy; alkylthio; acyl; free, salified or esterified carboxy; cyano; nitro; amino optionally substituted by one or more identical or different alkyl radicals; or cycloalkyl or aryl, the cycloalkyl and aryl radicals being optionally substituted by one or more identical or different radicals chosen from halogen atoms, the hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro or amino radicals optionally substituted by one or more identical or different alkyl radicals; represent, independently, a hydrogen atom or an alkyl, alkenyl or alkynyl radical, or more identical or different radicals, chosen from halogen atoms; the substituents hydroxy; alkoxy; alkylthio; acyl; free, salified or esterified carboxy; cyano; nitro; amino optionally substituted by one or more identical or different alkyl radicals; or cycloalkyl or aryl, the cycloalkyl and aryl radicals being optionally substituted by one or more identical or different radicals, chosen from halogen atoms, the substituents hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro or amino optionally substituted by one or more identical or different alkyl radicals; one or more identical or different radicals, chosen from halogen atoms; the substituents hydroxy; alkoxy; alkylthio; acyl; free, salified or esterified carboxy; cyano; nitro; amino optionally substituted by one or more identical or different alkyl radicals; or cycloalkyl or aryl, the cycloalkyl and aryl radicals being optionally substituted by one or more identical or different radicals, chosen from halogen atoms, the substituents hydroxy, alkyl, alkenyl, acyl, free, salified or esterified carboxy, alkoxy, alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro or amino optionally substituted by one or more identical or different alkyl radicals; radicals being optionally substituted by one or more identical or different substituents, chosen from halogen atoms, the substituents hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro or amino optionally substituted by one or more identical or different alkyl radicals; different substituents, chosen from halogen atoms, the substituents hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, acyl, free, salified or esterified carboxy, cyano, nitro or amino optionally substituted by one or more identical or different alkyl radicals; excluding the compound, in racemic form, in which R represents the amino radical, R' represents the 2-thienyl radical and R" represents the methyl radical.
In the expressions indicated above, the expression halogen represents a fluroine, chlorine, bromine or iodine atom, preferably chlorine.
The term alkyl designates a linear or branched alkyl radical comprising 1 to 12 carbon atoms. Preferably, the term alkyl represents a linear or branched alkyl radical having 1 to 6 carbon atoms, and in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, pentyl, isopentyl, hexyl, isohexyl radicals.
The term alkenyl designates a linear or branched alkenyl radical comprising 1 to 12 carbon atoms. Preferably, the term alkenyl represents a linear or branched alkenyl radical having 1 to 6 carbon atoms, and in particular the vinyl, allyl, propenyl, butenyl,
REFERENCES:
patent: 4138137 (1979-02-01), Pigerol et al.
Michaud et al, "Homochiral . . . Receptor Sites", European Journal of Medicinal Chemistrychimica Therapeutica, vol. 29, No. 11, 1994 Paris, France, pp. 869-876.
Ouyang et al, Syntheses . . . Calcium Ionophore, Chemical Abstracts, & Nucl. Med. Biol. vol. 125, No. 5, Jul. 29, 1996, Abstract No. 52501.
Vol. 23, No. 3, 1996, pp. 315-324.
Mousseron et al, "Syntheses . . . La Phencyclidine", Chimica Therapeutica, vol. 3, No. 4, 1968, Paris, France, pp. 241-247.
Kalir et al, "1-Phenylcycloalkylamine Derivatives. III", Chemical Abstracts, vol. 85, No. 3, Jul. 19, 1976, Abstract No. 13673 & Isr. J. Chem., vol. 13, No. 2, 1975, Israel, pp. 125-136.
Cazaux Jean-Bernard
Dafniet Michel
Kamenka Jean-Marc
Manginot Eric
Lambkin Deborah C.
Societe d'Expansion Scientifique Expansia
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