C16 unsaturated FP-selective prostaglandins analogs

A kind of technology selected from, compound, be applied in described new prostaglandin F analog, new prostaglandin F analog field

Inactive Publication Date: 2002-11-27
THE PROCTER & GAMBLE COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many prostaglandin analogs are available, there is still a need for more potent and selective prostaglandin analogs for the treatment of various diseases

Method used

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  • C16 unsaturated FP-selective prostaglandins analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 13,14-Dihydro-16-17-Z-didehydro-17-(2-fluorophenyl)prostaglandin F 1α preparation of a. Methyl 7-(2-oxo-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopent-1-enyl)heptanoate (E1b):

[0059] CH 2 Cl 2 2,6-Lutidine (1.3 equivalents) was added dropwise to the solution over 15 minutes. The solution was incubated at -78°C. TBDMS triflate (Triflate) (1.2 equiv) in CH 2 Cl 2 solution. The reaction was gradually warmed to room temperature and stirred at room temperature for 15 hours. 10% aqueous HCl solution was added, and the layers were separated. use CH 2 Cl 2 The aqueous layer was extracted, and the organic layers were combined. The organic layer was washed with brine, dried (Na 2 SO 4 ), and condensed. The residue was distilled under vacuum (10 mmHg) to obtain silyl ether E1b. b. 7-(5-but-3-enyl-2-hydroxyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoic acid methyl ester ( E1c):

[0060] To a THF slurry of Mg powder (2 eq.) was added crystalline iod...

Embodiment 2-17

[0067] Examples 2-17 were prepared with reference to Example 1, substituting appropriate starting materials. Those skilled in the art can appropriately change the temperature, pressure, atmosphere, solvent or sequence of the reaction. In addition, those skilled in the art can appropriately use protecting groups to block side reactions or increase yield. All of the above modifications can be readily carried out by a skilled organic chemist and, therefore, fall within the scope of the present invention.

Embodiment 2

[0069] 13,14-Dihydro-16-17-E-didehydro-17-(2-fluorophenyl)-17-trinorprostaglandin F1α

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PUM

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Abstract

The present invention provides novel PGF analogs. In particular, the present invention relates to compounds of general formula I, wherein R1, X and Z are as described below. The present invention also includes optical isomers, diastereomers and enantiomers of the general formula, as well as their pharmaceutically acceptable salts, biohydrolyzable amides, esters and imides. The compounds of the present invention can be used to treat a variety of diseases, such as orthopedic diseases. Thus, the present invention also provides pharmaceutical compositions containing these compounds. The invention also provides methods of treating orthopedic disorders using the compounds or compositions of the invention.

Description

field of invention [0001] The present invention relates to novel analogues of natural prostaglandins. In particular, the present invention relates to novel prostaglandin F analogs. The invention also relates to methods of use of said novel prostaglandin F analogues. Preferred uses include for the treatment of orthopedic diseases and glaucoma. Background of the invention [0002] Natural prostaglandins (PGA, PGB, PGE, PGF and PGI) are C-20 unsaturated fatty acids. PGF 2α , that is, natural human prostaglandin F, characterized in that the C of the carbon aliphatic ring 9 and C 11 On is the hydroxyl group, C 5 and C 6 Between is a cis double bond, C 13 and C 14 between trans double bonds. Therefore, PGF 2α The general formula is: [0003] Analogs of natural prostaglandin F already exist in the art. For example, U.S. Patent 4,024,179, Bindra and Johnson, May 17, 1977, German Patent DT-002,460,990, Beck, Lerch, Seeger, and Teufel, July 1, 197...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/557A61K31/5575A61P1/00A61P9/12A61P13/10A61P15/00A61P17/00A61P19/00A61P19/08A61P19/10A61P27/02A61P27/06A61P27/16C07B53/00C07CC07C59/215C07C59/56C07C59/72C07C235/26C07C251/06C07C259/06C07C311/51C07C327/22C07C405/00C07D277/64C07D307/40C07D307/46C07D307/54C07D307/66C07D307/80C07D333/36C07D333/56C07D333/60
CPCC07C59/215C07C59/56C07C59/72C07C235/26C07C251/06C07C259/06C07C311/51C07C327/22C07C405/00C07D277/64C07D307/46C07D307/66C07D307/80C07D333/36C07D333/56C07C2601/08A61P1/00A61P13/10A61P15/00A61P17/00A61P19/00A61P19/08A61P19/10A61P27/02A61P27/06A61P27/16A61P9/12
Inventor M·A·德隆D·L·索珀J·A·沃斯B·德
Owner THE PROCTER & GAMBLE COMPANY
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