N-substituted glycerophosphoethanolamines
AssigneeClarion Pharmaceuticals Inc.
InventorsFriedrich Paltauf, Albin Hermetter, Rudolf Franzmair
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Abstract
The present invention relates to novel, therapeutically active fatty alkyl and alkenyl ether glycerophospholipids bearing a 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl substituent on the ethanolamine nitrogen, methods of using the compounds and pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing same. The novel, therapeutically active compounds and salts of the invention possess anti-tumor, anti-psoriatic, anti-inflammatory, and anti-asthma activities.
Claims30
An N-substituted glycerophosphoethanolamine of the formula:
- ##STR5## and the isomeric forms thereof;
- wherein R represents a substituted or unsubstituted straight or branched chain C.sub.14-20 alkyl or alkenyl, said substituent being one or more of halo, C.sub.1-3 alkoxy or cyano, provided that a double bond of said alkenyl does not involve the carbon atom of said alkenyl that is bonded to the oxygen of the glyceryl backbone;
- and R.sup.1 is 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl;
- and the pharmaceutically acceptable salts thereof.
1-O-n-Octadecyl-2-O-meth yl-glycero-3-phospho-N-[3-(2-imidazolinyl)-2-imidazolinyl]-ethanolamine.
1-O-n-Octadecyl-2-O-methyl-glycero-3-phospho-N-(2-imidazolinyl)-ethanola mine.
A method of treating a tumor in a mammal afflicted with same which comprises administering to said mammal an anti-tumor effective amount of an N-substituted glycerophosphoethanolamine of the formula:
- ##STR6## and the isomeric forms thereof;
- wherein R represents a substituted or unsubstituted straight or branched chain C.sub.14-20 alkyl or alkenyl, said substituent being one or more of halo, C.sub.1-3 alkoxy or cyano, provided that a double bond of said alkenyl does not involve the carbon atom of said alkenyl that is bonded to the oxygen of the glyceryl backbone;
- and R.sup.1 is 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl;
- and the pharmaceutically acceptable salts thereof.
A method of treating psoriasis in a mammal afflicted with same which comprises administering to said mammal an anti-psoriatic effective amount of an N-substituted glycerophosphoethanolamine of the formula:
- ##STR7## and the isomeric forms thereof;
- wherein R represents a substituted or unsubstituted straight or branched chain C.sub.14-20 alkyl or alkenyl, said substituent being one or more of halo, C.sub.1-3 alkoxy or cyano, provided that a double bond of said alkenyl does not involve the carbon atom of said alkenyl that is bonded to the oxygen of the glyceryl backbone;
- and R.sup.1 is 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl;
- and the pharmaceutically acceptable salts thereof.
A method of treating inflammation in a mammal afflicted with same which comprises administering to said mammal an anti-inflammatory effective amount of an N-substituted glycerophosphoethanolamine of the formula:
- ##STR8## and the isomeric forms thereof;
- wherein R represents a substituted or unsubstituted straight or branched chain C.sub.14-20 alkyl or alkenyl, said substituent being one or more of halo, C.sub.1-3 alkoxy or cyano, provided that a double bond of said alkenyl does not involve the carbon atom of said alkenyl that is bonded to the oxygen of the glyceryl backbone;
- and R.sup.1 is 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl;
- and the pharmaceutically acceptable salts thereof.
A pharmaceutical composition comprising an anti-tumor, anti-psoriatic or anti-inflammatory effective amount of an N-substituted glycerophosphoethanolamine of the formula:
- ##STR9## and the isomeric forms thereof;
- wherein R represents a substituted or unsubstituted straight or branched chain C.sub.14-20 alkyl or alkenyl, said substituent being one or more of halo, C.sub.1-3 alkoxy or cyano, provided that a double bond of said alkenyl does not involve the carbon atom of said alkenyl that is bonded to the oxygen of the glyceryl backbone;
- and R.sup.1 is 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl;
- and the pharmaceutically acceptable salts thereof;
- and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.