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US 7,388,029 B2Granted
Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
AssigneeDuke University
InventorsMitchell Anthony DeLong, John McMillan McIver, Robert Scott Youngquist
Life of this patent
Estimating the term…
Abstract
A method for treating hair loss in mammals uses compositions containing prostaglandin F analogs. The compositions can be applied topically to the skin. The compositions can arrest hair loss, reverse hair loss, and promote hair growth.
Claims20
A method of treating hair loss comprising administering to a mammal a composition comprising:
- A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of
- pharmaceutically acceptable salts and hydrates of the structures above;
- biohydrolyzable amides, esters, and imides of the structures above;
- optical isomers, diastereomers, and enantiomers of the structures above;
- and combinations thereof;
- wherein R1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR3, CH2OH, S(O)2R3, C(O)NHR3, C(O)NHS(O)2R4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms;
- R2 is selected from the group consisting of a hydrogen atom, a lower heterogenous group, and a lower monovalent hydrocarbon group;
- R3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- R4 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- X is selected from the group consisting of —C≡C—, a covalent bond, —CH═C═CH—, —CH═CH—, —CH═N—, —C(O)—, —C(O)Y—, —(CH2)n—, wherein n is 2 to 4, —CH2NH—, —CH2S—, and —CH2O—;
- Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH;
- and
- Z is selected from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group,
- with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R1 is C(O)OR3 and R3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then R2 is not hydrogen.
11 more elements
A method of treating hair loss comprising administering to a mammal a composition comprising:
- A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of
- pharmaceutically acceptable salts and hydrates of the structures above;
- biohydrolyzable amides, esters, and imides of the structures above;
- optical isomers, diastereomers, and enantiomers of the structures above;
- and combinations thereof;
- wherein R1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR3, CH2OH, S(O)2R3, C(O)NHR3, C(O)NHS(O)2R4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms;
- R2 is selected from the group consisting of a hydrogen atom, a lower heterogeneous group, and a lower monovalent hydrocarbon group;
- R3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- R4 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- X is selected from the group consisting of -C≡C-, a covalent bond, -CH═C═-CH-, -CH═CH-, -CH═N-, -C(O)-, -C(O)Y-, -(CH2)n-, wherein n is 2 to 4, -CN2NH-, -CH2S-, and -CH2)-;
- Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH;
- and
- Z is selcted from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group,
- with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R1 is C(O)OH or C(O)OR3 and R3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then X is selected from the group consisting of -C≡C-, -CH═C═CH-, -CH═CH- and -CH═N-.
11 more elements
A method of treating hair loss comprising administering to a mammal a composition comprising:
- A) an active ingredient selected from the group consisting of a prostaglandin F analog having a structure selected from the group consisting of
- pharmaceutically acceptable salts and hydrates of the structures above;
- biohydrolyzable amides, esters, and imides of the structures above;
- optical isomers, diastereomers, and enantiomers of the structures above;
- and combinations thereof;
- wherein R1 is selected from the group consisting of C(O)OH, C(O)NHOH, C(O)OR3, CH2OH, S(O)2R3, C(O)NHR3, C(O)NHS(O)2R4, tetrazole, a cationic salt moiety, a pharmaceutically acceptable amine or ester comprising 2 to 13 carbon atoms, and a biometabolizable amine or ester comprising 2 to 13 atoms;
- R2 is selected from the group consisting of a hydrogen atom, a lower heterogeneous group, and a lower monovalent hydrocarbon group;
- R3 is selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- R4 selected from the group consisting of a monovalent hydrocarbon group, a heterogeneous group, a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted monovalent hydrocarbon group, a substituted heterogeneous group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group;
- X is selected from the group consisting of -C≡C-, a covalent bond, -CH═C═CH-, -CH═CH-, -CH═N-, -C(O)-, -C(O)Y-, -(CH2)n-, wherein n is 2 to 4, -CH2NH-, -CH2S-, and -CH2)-;
- Y is selected from the group consisting of a sulfur atom, an oxygen atom, and NH;
- and
- Z is selected from the group consisting of a carbocyclic group, a heterocyclic group, an aromatic group, a heteroaromatic group, a substituted carbocyclic group, a substituted heterocyclic group, a substituted aromatic group, and a substituted heteroaromatic group,
- with the proviso that when the bond at the C2-C3 position is a single bond, the bond at the C5-C6 position is a double bond, R1 is C(O)OH or C(O)OR3 and R3 is a monovalent hydrocarbon group or substituted monovalent hydrocarbon group, then Z is selected from the group consisting of a heterocyclic group, a substituted heterocyclic group and a substituted heteroaromatic group.
11 more elements
Dependencies are inferred from the claim text.