Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-07-05
2003-12-02
Krass, Frederick (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S841000, C514S843000, C514S931000, C514S934000, C514S944000, C514S967000, C544S158000, C544S173000, C564S292000
Reexamination Certificate
active
06656936
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention generally relates to novel acylcarnitine analogues and their use as topical, microbicidal spermicides. The acylcarnitine analogues are excellent spermicides, growth inhibitors of
Candida albicans
, and anti-HIV agents.
2. Background of the Invention
Many women want to control their fertility and reduce their risk of becoming infected with a sexually transmitted disease (STD). The AIDS epidemic has intensified the need for female-controlled methods that provide effective protection against both pregnancy and STDs (Irwin et al. 1998). No currently available agent simultaneously protects against both pregnancy and infection. There is a need to develop safe prophylactic agents that are spermicidal and display activity against HIV and STD pathogens.
Nonoxynol-9 (N-9), a nonionic surfactant, is the most widely used spermicides in the United States. Unfortunately, it does not appear to reduce the incidence of HIV infection (Rowe, 1997; Hira et al. 1997; Martin et al., 1997; Roddy et al. 1998). In fact, it has been demonstrated that N-9 actually increases the risk of genital inflammation (Stafford et al., 1998), urinary tract infections (Fihn et al., 1996), vulvovaginal candidiasis (Geiger and Foxman, 1996), and genital ulcers (Feldblum. 1996). One Canadian province no longer recommends the use of N-9 in any form (Rekart, 1992). Furthermore, N-9 is a mixture of oligomers (Yu and Chien, 1995) which may not meet future regulations as the health-care industry moves toward using pure compounds or mixtures whose individual components have met safety standards. For reasons of environmental toxicity (Thiele et al. 1997), several European nations have banned or restricted the use of N-9 and related compounds, sparking a debate (Renner, 1997) about the health risks of N-9. Clearly, other alternatives to N-9 as a microbicidal spermicide are needed.
It would be of benefit to have available an agent which displayed both spermicidal and anti-STD properties, particularly if the agent was non-irritating and did not increase the risk of inflammation and infection. It would be especially of benefit if the agent was active against the devastating disease of AIDS.
SUMMARY OF THE INVENTION
It is an object of this invention to provide acylcarnitine analogues of the general formula
wherein R is an alkyl chain having 10-30 carbons. In the preferred embodiment R is selected from the group consisting of —C
10
H
21
, —C
11
H
23
, —C
12
H
25
, —C
13
H
27
, —C
14
H
29
, —C
16
H
33
, —C
17
H
35
, —C
18
H
37
, —C
19
H
39
, —C
20
H
41
, —C
21
H
43
and —C
22
H
45
.
It is a further object of the instant invention to provide a composition of matter comprising a carrier and an acylcarnitine analogue of the general formula depicted in Formula 1 wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
, and where R is preferably —C
10
H
21
to —C
22
H
45
. The composition of matter may further comprise an acid. In a preferred embodiment, the acid is mucic acid. The carrier may be a gel.
The instant invention also provides a method of contraception for a female mammal. In a preferred embodiment, a contraceptively effective amount of a microbicidal spermicide comprising an acylcarnitine analogue as depicted in Formula 1, wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
, is placed in the vaginal cavity of the female mammal. The microbicidal spermicide may be a gel, and may further comprise an acid such as mucic acid.
The present invention also provides a method of inactivating mammalian spermatozoa, comprising contacting the spermatozoa with a spermicidally effective amount of a compound comprising an acylcarnitine analogue of the general formula depicted in Formula 1, wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
. In a preferred embodiment, R=—C
10
H
21
to —C
22
H
45
. The compound may be a gel, and may further comprise an acid such as mucic acid.
The present invention also provides a method of neutralizing human immunodeficiency virus, comprising contacting a human immunodeficiency virus with an effective amount of a compound comprising an acylcarnitine analogue of the general formula depicted in Formula 1, wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
. In a preferred embodiment, R=—C
10
H
21
to —C
22
H
45
. The compound may be a gel, and may further comprise an acid such as mucic acid.
The present invention also provides a method of inhibiting growth of
Candida albicans
, comprising contacting
Candida albicans
with an effective amount of a compound comprising an acylcarnitine analogue of the general formula depicted in Formula 1, wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
. In a preferred embodiment, R=—C
10
H21 to —C
22
H
45
. The compound may be a gel, and may further comprise an acid such as mucic acid.
The present invention also provides a method for simultaneously inactivating mammalian spermatozoa, neutralizing human immunodeficiency virus, and inhibiting growth of
Candida albicans
in a female mammal in need thereof, comprising administering intravaginally to a female mammal a quantity of a microbicidal spermicide sufficient to inactivate mammalian spermatozoa, neutralize human immunodeficiency virus, and inhibit growth of
Candida albicans
in said female mammal. The microbicidal spermicide comprises an acylcamitine analogue of the general formula depicted in Formula 1, wherein R is an alkyl chain selected from the group consisting of —C
10
H
21
to —C
30
H
61
. In a preferred embodiment, R=—C
10
H
21
to —C
22
H
45
. The compound may be a gel, and may further comprise an acid such as mucic acid.
REFERENCES:
patent: 5196418 (1993-03-01), Gandour et al.
Chemical Abstract 118:80881, “Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-l in intact mitochondria”, Gandour et al (1993).
Doncel Gustavo F.
Gandour Richard D.
Savle Prashant S.
Krass Frederick
Virginia Tech Intellectual Properties Inc.
Whitham Curtis & Christofferson, P.C.
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