Immunostimulating 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives
AssigneeJanssen Pharmaceutica NV
InventorsAlfons H. M. Raeymaekers, Leopold F. C. Roevens, Willy J. C. Van Laerhoven, Jean P. F. Van Wauwe
Life of this patent
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Abstract
The present invention relates to novel 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives having immunostimulating properties, which are useful for treating humans and warm-blooded animals suffering from disorders and/or diseases wherein the immune system is impaired or suppressed. Processes of preparing said novel compounds and compositions containing the same as active ingredient.
Claims20
A compound of the formula:
- ##STR36## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein:
- Ar is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, mercapto, C.sub.1-6 alkylthio, C.sub.1-6 alkyl, nitro, amino, mono- and di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkylcarbonylamino, arylcarbonylamino, C.sub.1-6 alkylsulfonylamino, trifluoromethyl, cyano, aminocarbonyl, mono- and di(C.sub.1-6 alkyl)aminocarbonyl, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, carboxaldehyde and hydroxymethyl;
- pyridinyl;
- thienyl;
- furanyl or furanyl substituted with C.sub.1-6 alkyl or halo;
- R.sup.1 is C.sub.3-10 alkyl, (C.sub.3-7 cycloalkyl)C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, aryl or (aryl)C.sub.1-6 alkyl;
- R.sup.2 is hydrogen, C.sub.1-20 alkyl, (C.sub.3-7 cycloalkyl)C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, aryl or (aryl)C.sub.1-6 alkyl;
- or R.sup.1 and R.sup.2 together may form a C.sub.3-6 alkandiyl radical;
- wherein in the foregoing each aryl independently is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, C.sub.1-6 alkyl, nitro, amino, trifluoromethyl or cyano.
An immunostimulating composition comprising an inert carrier and as active ingredient an effective immunostimulating amount of a compound of the formula:
- ##STR37## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein:
- Ar is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, mercapto, C.sub.1-6 alkylthio, C.sub.1-6 alkyl, nitro, amino, mono- and di(C.sub.1-6 -alkyl)amino, C.sub.1-6 alkylcarbonylamino, arylcarbonylamino, C.sub.1-6 alkylsulfonylamino, trifluoromethyl, cyano, aminocarbonyl, mono- and di(C.sub.1-6 alkyl)aminocarbonyl, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, carboxaldehyde and hydroxymethyl;
- pyridinyl;
- thienyl;
- furanyl or furanyl substituted with C.sub.1-6 alkyl or halo;
- R.sup.1 is C.sub.3-10 alkyl, (C.sub.3-7 cycloalkyl)C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, aryl or (aryl)C.sub.1-6 alkyl;
- R.sup.2 is hydrogen, C.sub.1-20 alkyl, (C.sub.3-7 cycloalkyl)C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, aryl or (aryl)C.sub.1-6 alkyl;
- or R.sup.1 and R.sup.2 together may form a C.sub.3-6 alkandiyl radical;
- wherein in the foregoing each aryl independently is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, C.sub.1-6 alkyl, nitro, amino, trifluoromethyl or cyano.
A method of treating humans and warm-blooded animals suffering from disorders or diseases wherein the immune system is impaired, said method comprising the systemic administration to said humans and warm-blooded animals of an effective immunostimulating amount of a compound of the formula:
- ##STR38## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein:
- Ar is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, mercapto, C.sub.1-6 alkylthio, C.sub.1-6 alkyl, nitro, amino, mono- and di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkylcarbonylamino, arylcarbonylamino, C.sub.1-6 alkylsulfonylamino, trifluoromethyl, cyano, aminocarbonyl, mono- and di(C.sub.1-6 alkyl)aminocarbonyl, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, carboxaldehyde and hydroxymethyl;
- pyridinyl;
- thienyl;
- furanyl or furanyl substituted with C.sub.1-6 alkyl or halo;
- R.sup.1 and R.sup.2 each independently are C.sub.1-20 alkyl, (C.sub.3-7 cycloalkyl)C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, aryl or (aryl)C.sub.1-6 alkyl;
- and one of R.sup.1 and R.sup.2 may also be hydrogen;
- or R.sup.1 and R.sup.2 together may form a C.sub.3-6 alkandiyl radical;
- wherein in the foregoing each aryl independently is phenyl optionally substituted with from 1 to 3 substituents each independently selected from halo, hydroxy, C.sub.1-6 alkyloxy, C.sub.1-6 alkyl, nitro, amino, trifluoromethyl or cyano.
Dependencies are inferred from the claim text.