Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents

• US 8,017,655 B2
• Filed: 12/19/2008
• Issued: 09/13/2011
• Est. Priority Date: 09/21/1992
• Status: Expired due to Fees

• Current Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Original Assignee: Allergan, Inc. (Canada) (Abbvie Incorporated)
• Inventors: Woodward, David F., Burk, Robert M., Andrews, Steven W., Garst, Michael E.
• Primary Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US12/339,494
• Publication Number:
  US 20090227672A1
• Time in Patent Office: 998 Days
• Field of Search: 514/530, 514/555, 514/570, 514/913, 514/622, 560/55, 562/465, 564/171
• US Class Current: 514/622
• 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: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/06 Antiglaucoma agents or miotics
• 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 present invention provides cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl compounds, which may be substituted in the 1-position with amino, amido, ether or ester groups, e.g., a 1-OH cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compound. The cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma. Moreover, the cyclopentane heptanoic, 2-(cycloalkyl or arylalkyl) compounds of this invention are smooth muscle relaxants with broad application in systemic hypertensive and pulmonary diseases; smooth muscle relaxants with application in gastrointestinal disease, reproduction, fertility, incontinence, shock, etc.

Claims

1. A pharmaceutical composition comprising cyclopentane N-ethyl hepteneamide-5-cis-2-(3α

-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1_α

2_β

3_α

5_α

], benzalkonium chloride, and sodium chloride as a tonicity agent.

2. The pharmaceutical composition of claim 1, wherein the composition is for ophthalmic application.

3. The pharmaceutical composition of claim 2, wherein the composition is packaged in a dropper for ophthalmic application.

4. The pharmaceutical composition of claim 1, wherein the pH of the composition is 4.5-7.5.

5. The pharmaceutical composition of claim 1, for use in lowering intraocular pressure of the eye.

6. The pharmaceutical composition of claim 1, for treatement of glaucoma.