Substituted cyclopentanes for inducing hair growth

Patent metadata

Field	Value
Publication number	US-9499478-B2
Application number	US-201414488093-A
Country	US
Kind code	B2
Filing date	Sep 16, 2014
Priority date	Feb 14, 2011
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

Provided herein, inter alia, are, methods of using esters of bimatoprost with the Formula (I):

First claim

What is claimed is:

1. A method for inducing hair growth in a subject, comprising administering to a subject in need thereof a therapeutically effective amount of a compound of Formula (I):

or a stereoisomer thereof;
wherein
R 1 is hydrogen or R la C(O)-;
R 2 is hydrogen or R 2a C(O)-;
R 3 is hydrogen or R 3a C(O)-;
R 1a , R 2a and R 3a are independently C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, or aryl, wherein each of C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, or aryl may be unsubstituted or have one or more substituent groups; and
R 4 and R 5a are independently C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, or aryl, wherein each of C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, or aryl may be unsubstituted or have one or more substituent groups;
wherein the one or more substituent groups are selected from the group consisting of:
(A) OH, NH 2 , SH, CN, CF 3 , NO 2 , oxo, halogen, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, and unsubstituted heteroaryl, and
(B) alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, substituted with at least one substituent selected from:
(i) oxo, OH, NH 2 , SH, CN, CF 3 , NO 2 , halogen, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, and unsubstituted heteroaryl, and
(ii) alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, substituted with at least one substituent selected from:
(a) oxo, OH, NH 2 , SH, CN, CF 3 , NO 2 , halogen, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, and unsubstituted heteroaryl, and
(b) alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, substituted with at least one substituent selected from oxo, OH, NH 2 , SH, CN, CF 3 , NO 2 , halogen, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl, unsubstituted aryl, and unsubstituted heteroaryl;

provided that at least one of R 1 , R 2 and R 3 is not hydrogen.

2. The method of claim 1 , wherein said administering is topical administering.

3. The method of claim 2 , wherein said administering is topical epidermal administering.

4. The method of claim 1 , wherein said subject suffers from alopecia.

5. The method of claim 1 , wherein said subject is in need of hair growth of the cilia, the supercilia, scalp pili, or body pili.

6. The method of claim 1 , wherein said compound is of Formula (IIIb)

7. The method of claim 1 , wherein said compound is of Formula (IVa)

8. The method of claim 1 , wherein said compound is of Formula (IVb)

Assignees

• Allergan Inc

Inventors

• Woodward David F
• Wang Jenny W
• Poloso Neil J
• Gac Todd S
• Burk Robert M
• Garst Michael E

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61Q7/00

  Preparations for affecting hair growth · CPC title

• C07C405/0041

  containing nitrogen · CPC title

• C07C405/00 Primary

  Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins {; Analogues or derivatives thereof} · CPC title

• A61K8/42 Primary

  Amides · CPC title