Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ether doai
Reexamination Certificate
1999-03-22
2001-08-28
Keys, Rosalynd (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ether doai
C514S843000, C514S967000, C568S608000, C568S610000, C424S078240, C424SDIG001
Reexamination Certificate
active
06281251
ABSTRACT:
TECHNICAL FIELD
The present invention relates to mono- and di-iodinated nonoxynol-9-derivatives and methods for their use.
BACKGROUND ART
Nonionic surfactants are a preferred class of active agents for use in spermicidal formulations. For example, the nonionic surfactant nonoxynol-9 is a component in many commercially available spermicidal formulations. Spermicidal formulations are administered in the vaginal cavity for their local activity against human spermatozoa. It has been theorized that spermicidal agents exert their activity by inserting a hydrophobic moiety into the spermatozoan cell membrane. Upon insertion, the spermicidal agents disrupt the integrity of the cell membrane. This leads to an osmotic imbalance in the cell and, ultimately, cell lysis, thereby preventing sperm from fertilizing the egg and impeding conception.
Mixed experimental evidence exists as to whether non-ionic surfactants used in spermicides kill human immunodeficiency virus (HIV). In vitro experiments reveal that nonoxynol-9 inactivates HIV-1 completely. The inactivation may be through a mechanism similar to that proposed for the reduction of sperm motility. The hydrophobic portion of the nonoxynol-9 molecule may associate with hydrophobic fragments on the surface of the HIV virion leading to the derangement of the viral envelope and inactivation. The hydrophobic moieties of the virion include constituent lipids, sterols and proteins of the host cell membrane from which the viral envelope stems in addition to viral proteins.
Nonoxynol-9 suffers from a number of drawbacks. For example, in vivo clinical trials of products containing nonoxynol-9 do not show clear evidence of protection against HIV infection. Certain studies indicated that HIV infection rates were essentially equal when a population of women used vaginal contraceptives containing nonoxynol-9 or a placebo. Furthermore, vaginal irritation appears to increase with increased dose of nonoxynol-9.
A need exists for compounds which are more effective at lower doses, and which can achieve equal or greater contraceptive and anti-HIV efficacy with less irritation.
DISCLOSURE OF THE INVENTION
An advantage of the present invention is the provision of compounds which are effective to prevent conception.
Another advantage of the present invention is the provision of compounds which are effective to reduce or prevent transmission of sexually transmitted diseases.
Additional advantages of the present invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from the practice of the present invention. The advantages of the present invention may be realized and obtained as particularly pointed out in the appended claims.
According to the present invention, the foregoing and other advantages are achieved in part by a compound of the formula:
wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25.
Another aspect of the present invention is a pharmaceutical composition comprising a compound of formula (I), and a pharmaceutically acceptable carrier.
A further aspect of the present invention is a method for preventing conception, the method comprising the step of administering an effective amount of a compound of formula (I).
Yet another aspect of the present invention is a method for reducing or preventing transmission of a sexually transmitted disease, the method comprising the step of administering an effective amount of a compound of formula (I).
One more aspect of the present invention relates to plastic and paper products coated with compounds of formula (I).
An additional aspect of the present invention is a process for preparing a compound of formula (I), the process comprising the steps of reacting thallium trifluoroacetate with a compound of formula:
wherein R and n are as defined above to form an electrophilic thallium intermediate, and iodinating the intermediate.
Additional advantages of the present invention will become readily apparent to those skilled in this art from the following detailed description, wherein only the preferred embodiment of the present invention is shown and described, simply by way of illustration of the best mode contemplated for carrying out the present invention. As will be realized, the present invention is capable of other and different embodiments, and its several details are capable of modifications in various obvious respects, all without departing from the present invention. Accordingly, the drawings and description are to be regarded as illustrative in nature, and not as restrictive.
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Sander, et al., “A Practical Method for Testing the Spermicidal Action of Chemical Contraceptives,”Human Fertility, 6, pp. 134-137 (1941).
Resnick, et al., “Anti-HIV Screening Technology,” N. Alexander, H. Gabelnick, J. Spieler (eds.),Heterosexual Transmission of AIDS, pp. 311-326 (New York: Wiley-Liss, 1990).
Digenis George
Doncel Gustavo
Fowler Philip
Matsumoto Kazuya
Keys Rosalynd
McDermott & Will & Emery
University of Kentucky Research Foundation
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