4'-Substituted-4',5'-dihydropsoralens and therapeutical uses thereof

US6177424A · kind A · utility

Inventors

• Ned D. Heindel · Easton, US
• Jeffrey D. Laskin · Piscataway, US
• Marilyn S. Whittemore · Germantown, US
• Thomas E. McNeel · Memphis, US
• Christophe Guillon · Bethlehem, US
• Diane E. Heck · Rumson, US
• Robert Rapp · Johnstown, US

Key dates

• Filing date: Nov 30, 1999
• Grant date: Jan 23, 2001
• Expiry date: Nov 30, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to 4'-substituted-4',5'-dihydropsoralen compounds of formula(V): ##STR1## In the formula R is hydrogen, a halogen, CN or an acyl group; T is a halogen, CN, a carboalkoxy group NR.sup.1 R.sup.2, or (N.sup.+ R.sup.1 R.sup.2 R.sup.3)X.sup.-, R.sup.1 and R.sup.2 are independently a C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.2 together with the nitrogen form a 5-8 member heterocyclic ring, or when T is (N.sup.+ R.sup.1 R.sup.2 R.sup.3)X.sup.-, R.sup.1 and R.sup.2 together with the nitrogen form a 5-8 member heterocyclic ring or heterocyclic aromatic ring; R.sup.3 is hydrogen, a C.sub.1 -C.sub.12 alkyl, or, when R.sup.1 and R.sup.2 together with the nitrogen form a heterocyclic aromatic ring, R.sup.3 is a double bond within the heterocyclic aromatic ring; X.sup.- is a halide. In another embodiment, the invention relates to processes for preparing 4'-substituted-4',5'-dihydropsoralen compounds described above. The compounds of the invention have beneficial pharmaceutical properties and can be used alone or in pharmaceutical compositions used to treat a proliferative skin disorder and to treat microbial infections in a mammal by administering to the mammal an effect…