Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

• US 20040044045A1
• Filed: 07/15/2003
• Published: 03/04/2004
• Est. Priority Date: 09/21/1992
• Status: Abandoned Application

• Current Assignee: Allergan Incorporated (Abbvie Incorporated)
• Original Assignee: Allergan Incorporated (Abbvie Incorporated)
• Inventors: Burk, Robert M.
• Application Number:
  US10/621,195
• Publication Number:
  US 20040044045A1
• Time in Patent Office: Days
• US Class Current: 514/344
• CPC Class Codes: A61K 31/381 having five-membered rings
• CPC Class Codes: A61K 31/557 Eicosanoids, e.g. leukotrienes or prostaglandins
• CPC Class Codes: A61K 31/5575 having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
• CPC Class Codes: A61K 31/5585 having five-membered rings containing oxygen as the only ring hetero atom, e.g. prostacyclin
• CPC Class Codes: A61K 31/559 having heterocyclic rings containing hetero atoms other than oxygen
• CPC Class Codes: C07C 215/42 having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 247/10 and containing rings
• CPC Class Codes: C07C 255/36 the carbon skeleton being further substituted by hydroxy groups
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 35/21 polycyclic, at least one hydroxy group bound to a non-condensed ring
• CPC Class Codes: C07C 405/00 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

Abstract

The invention relates to the use of derivatives of F-type prostaglandins as ocular hypotensives. The PGF derivatives used in accordance with the invention are represented by the following formula I:

wherein wavy line attachments indicate either the alpha (α) or beta (β) configuration; dashed bonds represent a double bond, or a single bond, R is a substituted heteroaryl radical, R¹ is hydrogen or a lower alkyl radical having up to six carbon atoms, X is selected from the group consisting of —OR¹, —N(R¹)₂, R¹ is hydrogen or a lower alkyl radical having up to six carbon 20 atoms, X is selected from the group consisting of —OR¹, —N(R¹)₂ and —N(R⁵)SO₂R⁶, wherein R⁵ represents hydrogen or CH₂OR⁶ and R⁶ represents hydrogen or a lower alkyl radical having up to six carbon atoms and halogen substituted derivatives of said lower alkyl radical, e.g. a fluoro substituted lower alkyl radical; Y is ═O or represents 2 hydrogen radicals. Certain of the compounds represented by Formula I comprise another aspect of the present invention.

Claims

1. A method of treating ocular hypertension which comprises administering to a mammal having ocular hypertension a therapeutically effective amount of a compound represented by formula II:

2. The method of claim 1 wherein the substituent on the heteroaryl radical is selected from the group consisting of lower alkyl, halogen, trifluoromethyl, COR₁, COCF₃, SO₂NR₁, SO₂NH₂, NO₂ and CN.

3. A pharmaceutical product, comprising a container adapted to dispense the contents of said container in metered form;

and an ophthalmic solution in said container comprising a compound of formula I as defined in claim 1, or a pharmaceutically acceptable salt thereof, in admixture with a non-toxic, ophthalmically acceptable liquid vehicle.

4. A method of treating glaucoma which comprises administering to a mammal having glaucoma a therapeutically effective amount of a compound represented by formula I:

5. The method of claim 4 wherein said compound is represented by formula II:

6. A method of treating elevated intraocular pressure which comprises administering to a mammal having elevated intraocular pressure a therapeutically effective amount of a compound represented by formula I:

7. The method of claim 6 wherein said compound is represented by formula II: