4-(1-hydroxy-2-N-substituted sulfonamido) ethyl-5-hydroxy-2(5H)-

Details 4-(1-hydroxy-2-N-substituted sulfonamido) ethyl-5-hydroxy-2(5H)- 4-(1-hydroxy-2-N-substituted sulfonamido) ethyl-5-hydroxy-2(5H)-

1990-03-23

1992-01-14

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544229, 544337, 544379, 544383, 549214, 549313, 549318, C07D30760

Patent

active

050812610

ABSTRACT:
Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.* or PO(OR.sub.1.sup.*).sub.2 or PO(OR.sub.1.sup.*)R.sub.1.sup.* where R.sub.1.sup.* independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; R.sub.2 is H, alkyl of 1 to 20 carbons, or R.sub.2 and Y jointly represent a heterocycle which incorporates the sulfonamide nitrogen in the ring as a heteroatom; R.sub.3 is H or alkyl of 1 to 20 carbons; X is H, R.sub.4, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, CO--N--(R.sub.4).sub.2, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, and R.sub.4 independently is H, phenyl, substituted phenyl, alkyl of 1 to 20 carbons or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy, with a O--COR.sub.4.sup.* group or with a COR.sub.4.sup.* group where R.sub.4.sup.* is H, lower alkyl, OH, OR.sub.4.sup.**, NH.sub.2, NHR.sub.4.sup.** or N(R.sub.4.sup.**).sub.2 group where R.sub.4.sup.** independently is H or lower alkyl, with the proviso that when X is CO--O--R.sub.4 or is CO--NH--R.sub.4 then R.sub.4 is not hydrogen, and Y is H, phenyl or substituted phenyl, or alkyl of 1 to 20 carbons, or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy, O--PO(OR.sub.5).sub.2, O--PO(OR.sub.5)R.sub.5, O--SO.sub.3 H, O--SO.sub.2 R.sub.5, O--COR.sub.5, or COR.sub.5 group where R.sub.5 is H, lower alkyl, OH, OR.sub.5.sup.*, NH.sub.2, NHR.sub.5.sup.* or N(R.sub.5.sup.*).sub.2 group where R.sub.5.sup.* is lower alkyl, or R.sub.2 and Y jointly represent a heterocycle which incorporates the sulfonamide nitrogen in the ring as a heteroatom, with the proviso that when Y is an alkyl substituted with O--PO(OR.sub.5).sub.2 or with O--PO(OR.sub. 5)R.sub.5 then R.sub.5 is not OH, are disclosed. The compounds possess anti-inflammatory activity.

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