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US 2003/0166716 A1Published application
Lipoxins and aspirin-triggered lipoxins and their stable analogs in the treatment of asthma and inflammatory airway diseases
OwnerCharles N. Serhan, Bruce D. Levyinventors
Life of this patent
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Abstract
The use of lipoxin analogs for the treatment or prevention of asthma and asthma related diseases is described. In particular, acetylenic lipoxin analogs are effective for the treatment and prevention of eosinophil recruitment involved with the inflammation processes associated with asthma, asthma like conditions, and lung injuries associated from airway inflammation or infection as brought about by leukocyte-mediated injury from within.
Claims42
A method for treating or preventing disorders of the respiratory tract or lung comprising the step of administering to a subject in need thereof, a therapeutically effective amount of a lipoxin analog having the formula
- 42
- wherein X is R1, OR1, or SR1;
- wherein R1 is
- (i) a hydrogen atom;
- (ii) an alkyl of 1 to 8 carbon atoms, inclusive, which may be straight chain or branched;
- (iii) a cycloalkyl of 3 to 10 carbon atoms;
- (iv) an aralkyl of 7 to 12 carbon atoms;
- (v) phenyl;
- (vi) substituted phenyl
- 43
- wherein Z1, Zii, Ziii, Ziv and Zv are each independently selected from —NO2, —CN, —C(═O)—R1, —SO3H, a hydrogen atom, halogen, methyl, —ORx, wherein Rx is 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched, and hydroxyl;
- (vii) a detectable label molecule;
- or
- (viii) a straight or branched chain alkenyl of 2 to 8 carbon atoms, inclusive;
- wherein Q1 is (C═O), SO2 or (CN), provided when Q1 is CN, then X is absent;
- wherein Q3 and Q4 are each independently O, S or NH;
- wherein one of R2 and R3 is a hydrogen atom and the other is
- (a) H;
- (b) an alkyl of 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched;
- (c) a cycloalkyl of 3 to 6 carbon atoms, inclusive;
- (d) an alkenyl of 2 to 8 carbon atoms, inclusive, which may be straight chain or branched;
- or
- (e) RaQ2Rb wherein Q2 is —O— or —S—;
- wherein Ra is alkylene of 0 to 6 carbon atoms, inclusive, which may be straight chain or branched and wherein Rb is alkyl of 0 to 8 carbon atoms, inclusive, which may be straight chain or branched, provided when Rb is 0, then Rb is a hydrogen atom;
- wherein R4 is
- (a) H;
- (b) an alkyl of 1 to 6 carbon atoms, inclusive, which may be a straight chain or branched;
- wherein R5 is
- 44
- wherein Zi, Zii, Ziii, Ziv and Zv are each independently selected from —NO2, —CN, —C(═O)—R1, —SO3H, a hydrogen atom, halogen, methyl, —ORx, wherein Rx is 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched, and hydroxyl or a substituted or unsubstituted, branched or unbranched alkyl group;
- wherein Y1 is —OH, methyl, —SH, an alkyl of 2 to 4 carbon atoms, inclusive, straight chain or branched, an alkoxy of 1 to 4 carbon atoms, inclusive, or CHaZb where a+b=3, a=0 to 3, b=0 to 3 and Z is cyano, nitro or a halogen;
- wherein R6 is
- (a) H;
- (b) an alkyl from 1 to 4 carbon atoms, inclusive, straight chain or branched;
- wherein T is O or S, and pharmaceutically acceptable salts thereof, thereby treating or preventing disorders of the respiratory tract or lung in the subject.
32 more elements
A packaged pharmaceutical composition for treating or preventing disorders of the respiratory tract or lung in a subject, comprising a container holding a therapeutically effective amount of at least one lipoxin analog having the formula
- 45
- wherein X is R1, OR1, or SR1;
- wherein R1 is
- (i) a hydrogen atom;
- (ii) an alkyl of 1 to 8 carbon atoms, inclusive, which may be straight chain or branched;
- (iii) a cycloalkyl of 3 to 10 carbon atoms;
- (iv) an aralkyl of 7 to 12 carbon atoms;
- (v) phenyl;
- (vi) substituted phenyl
- 46
- wherein Zi, Zii, Ziii, Ziv and Zv are each independently selected from —NO2, —CN, —C(═O)—R1, —SO3H, a hydrogen atom, halogen, methyl, —ORx, wherein Rx is 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched, and hydroxyl;
- (vii) a detectable label molecule;
- or
- (viii) a straight or branched chain alkenyl of 2 to 8 carbon atoms, inclusive;
- wherein Q1 is (C═O), SO2 or (CN), provided when Q1 is CN, then X is absent;
- wherein Q3 and Q4 are each independently O, S or NH;
- wherein one of R2 and R3 is a hydrogen atom and the other is
- (a) H;
- (b) an alkyl of 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched;
- (c) a cycloalkyl of 3 to 6 carbon atoms, inclusive;
- (d) an alkenyl of 2 to 8 carbon atoms, inclusive, which may be straight chain or branched;
- or
- (e) RaQ2Rb wherein Q2 is —O— or —S—;
- wherein Ra is alkylene of 0 to 6 carbon atoms, inclusive, which may be straight chain or branched and wherein Rb is alkyl of 0 to 8 carbon atoms, inclusive, which may be straight chain or branched, provided when Rb is 0, then Rb is a hydrogen atom;
- wherein R4 is
- (a) H;
- (b) an alkyl of 1 to 6 carbon atoms, inclusive, which may be a straight chain or branched;
- wherein R5 is
- 47
- wherein Zi, Zii, Ziii, Ziv and Zv are each independently selected from —NO2, —CN, —C(═O)—R1, —SO3H, a hydrogen atom, halogen, methyl, —ORx, wherein Rx is 1 to 8 carbon atoms, inclusive, which may be a straight chain or branched, and hydroxyl or a substituted or unsubstituted, branched or unbranched alkyl group;
- wherein Y1 is —OH, methyl, —SH, an alkyl of 2 to 4 carbon atoms, inclusive, straight chain or branched, an alkoxy of 1 to 4 carbon atoms, inclusive, or CHaZb where a+b=3, a=0 to 3, b=0 to 3 and Z is cyano, nitro or a halogen;
- wherein R6 is
- (a) H;
- (b) an alkyl from 1 to 4 carbon atoms, inclusive, straight chain or branched;
- wherein T is O or S, and pharmaceutically acceptable salts thereof;
- and instruction for treating or preventing disorders of the respiratory tract or lung in the subject.
33 more elements
Dependencies are inferred from the claim text.