Secondary amines as therapeutic agents

Patent metadata

Field	Value
Publication number	US-9388153-B2
Application number	US-201414565817-A
Country	US
Kind code	B2
Filing date	Dec 10, 2014
Priority date	Dec 20, 2013
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Compounds such as those represented by Formulas 1-6 can be used in topical liquids, creams, or other dosage forms such as solids, for reducing intraocular pressure, treating glaucoma, growing hair, or other medical uses.

First claim

What is claimed is:

1. A compound represented by a formula:

wherein B is optionally substituted phenyl;
W is CH 2 , O, S, or NH;
a is 2;
X is NR 1 or O;
L is —CH 2 O-A-, —CH 2 CH 2 -A-, —CH═CH-A-, -A-OCH 2 —, -A-CH 2 CH 2 —, or -A-CH═CH—;
A is an optionally substituted interarylene, an optionally substituted interheteroarylene, or —(CH 2 ) 3 —;
R 1 is H, C 1-6 alkyl, or COCH 3 ;
R 2 , R 3 , and R 4 are independently H, or a substituent having a molecular weight of 15 g/mol to 100 g/mol; and
Q is CO 2 R 5 , CH 2 OR 5 , CONR 5 R 6 , or optionally substituted tetrazol-5-yl, wherein R 5 and R 6 are independently H, C 1-6 alkyl, C 1-6 hydroxyalkyl, or optionally substituted phenyl.

2. The compound of claim 1 , wherein R 2 is H.

3. The compound of claim 1 , wherein R 3 is H.

4. The compound of claim 1 , wherein R 4 is H.

5. The compound of claim 1 , wherein W is CH 2 .

6. The compound of claim 1 , wherein W is O.

7. The compound of claim 1 , wherein X is NR 1 .

8. The compound of claim 7 , wherein R 1 is H.

9. The compound of claim 7 , wherein R 1 is C 1-3 alkyl, or COCH 3 .

10. The compound of claim 1 , wherein X is O.

11. The compound of claim 1 , wherein L is -A-OCH 2 —.

12. The compound of claim 1 , wherein A is interphenylene.

13. The compound of claim 1 , wherein Q is CO 2 R 5 .

14. The compound of claim 1 , wherein Q is CH 2 OH.

15. The compound of claim 1 , wherein B is 3-fluorophenyl.

16. The compound selected from the group consisting of:

17. An ophthalmic liquid comprising a compound according to claim 1 and a pharmaceutically acceptable excipient.

18. A solid dosage form comprising a compound according to claim 1 and a pharmaceutically acceptable excipeint.

19. An ophthalmic liquid comprising a compound according to claim 16 and a pharmaceutically acceptable excipient.

20. A solid dosage form comprising a compound according to claim 16 and a pharmaceutically acceptable excipient.

21. A method of reducing intraocular pressure comprising administering a compound according to claim 1 to a mammal in need thereof.

22. A method or growing hair comprising administering a compound according to claim 1 to a mammal in which hair growth is desirable.

23. A method of reducing intraocular pressure comprising administering a compound according to claim 16 to a mammal in need thereof.

24. A method for growing hair comprising administering a compound according to claim 16 to a mammal in which hair growth is desirable.

Assignees

• Allergan Inc

Inventors

• Ngo Vinh X
• Old David W

Classifications

• C07C233/81

  having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups · CPC title

• C07D307/82 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring · CPC title

• C07C217/84

  the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom · CPC title

• A61K31/136

  having the amino group directly attached to the aromatic ring, e.g. benzeneamine · CPC title

• A61K31/196

  the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil · CPC title