Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
1999-11-10
2002-04-09
Peselev, Elli (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S023000, C514S089000, C514S092000, C536S004100, C536S018700, C536S123000, C546S301000
Reexamination Certificate
active
06369042
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel antioxidative Vitamin B
6
analogs and their use in the cosmetic, dermatological, pharmaceutical and/or nutritional fields.
BACKGROUND
Skin is subject to insults by many extrinsic and intrinsic factors. Extrinsic factors include ultraviolet radiation (e.g., from sun exposure), environmental pollution, wind, heat, low humidity, harsh surfactants, abrasives, and the like. Intrinsic factors include chronological aging and other biochemical changes from within the skin. Whether extrinsic or intrinsic, these factors result in visible signs of skin aging and environmental damage, such as wrinkling and other forms of roughness (including increased pore size, flaking and skin lines), and other histological changes associated with skin aging or damage.
In recent years, intrinsic factors contributing to the premature aging of skin have been investigated. Substances having anti-oxidizing activity, those having an activity of scavenging reactive oxygen species or radicals, or an activity of inhibiting the generation of reactive oxygen species in the presence of a metal ion (Fenton reaction) have attracted attention, because reactive oxygen species or radicals are responsible for a variety of diseases as well as the aging of skin such as hardening, development of wrinkles and pigmentation, and the generation of reactive oxygen species in the presence of metal ion causes the oxidative disorders in the body which are responsible for a variety of diseases and the aging of skin described above.
Additionally, free radicals also have been associated with the development of tumors. It is believed that free radicals damage DNA and change the normal cells into potential tumor cells.
One effort to reduce the signs of aging that has received attention in recent years is the use of alpha-hydroxy acids (AHAs). Products with AHAs are marketed for a variety of purposes: to smooth fine lines and surface wrinkles, to improve skin texture and tone, to unblock and cleanse pores, to improve oily skin or acne, and to improve skin condition in general. Cosmetics that contain AHAs have become widely used in recent years despite many unanswered questions about their safety. Recently, a study sponsored by the cosmetics industry indicates that these products may make users more sensitive to sunlight and especially to the ultraviolet (UV) radiation component of sunlight. UV exposure can damage the skin and at high doses, especially over a long period, can cause skin cancer. Thus, it would be advantageous, for example, for cosmetics containing alpha-hydroxy acids to contain a UV protectant.
Patient compliance refers to the extent to which actual behaviour of a patient coincides with medical advice. Approximately two-thirds of patients do not follow their doctor's advice. Some of the reasons for not taking the medication as prescribed are complexity of drug regimen, embarrassment, e.g., children who need to take medications at school, and forgetfulness. Thus, an easy method of treatment of diseases would be desirable.
Thus, it would be desirable to have a compound that is easily applied or administered which would provide (1) benefit to the skin, (2) treatment of diseases, (3) an advantageous means of drug/vitamin delivery and/or (4) cosmotological enhancements.
SUMMARY OF THE INVENTION
The invention concerns new vitamin B
6
analogs with antioxidative, radical-scavenging functions which counteract pathophysiological disorders especially connected with aging processes. The new agents counteract against oxidation- and age-mediated, acquired and inherited disease-related pathophysiological disorders. These functions render the new analogs useful for the treatment of these disorders which include but are not limited to multiple sclerosis, degenerative cell, tissue and organ processes, gerontological diseases such as Alzheimer's disease, Diabetes Type I, allergies, neurological disorders, skin diseases such as psoriasis, bone and bone tissue disorders such as osteoporosis. The new analogs are also antidotes against organo-phosphorous compounds.
The new compounds are also suitable for the treatment of disorders associated with defects of the vitamin B
6
metabolism and therefore act as vitamin B
6
antagonists.
The analogs of this invention have important anti-infective potential, for example antiviral activity, antiparasitic activity, and antifungal activity. Especially useful are the analogs of the invention for the treatment of viral diseases caused by enveloped viruses such as hepatitis, herpes and retro viruses but are also useful for the treatment of other viral infections, such as infection from influenza or rhinovirus.
The new agents have cytoprotecting, immunomodulating, stimulating and inhibiting activity in vitro, suppress cell proliferation in cancer cells and cause cell death in these cells.
These functions enable the new compounds to be useful for cosmetic or cosmeceutical or nutritional applications, keratological or skin-caring applications such as skin protection and skin restoration, in improving health, fitness, hygiene of the human and animal body, skin, teeth, oral gums, nails, lips and hair. The new analogs are also useful agents for the treatment and prevention of sun or skin bums. In addition, the new analogs may be used as protecting dyes. The new analogs are also useful agents for the release of vitamins. They aid in the transport of pharmaceutical, cosmeceutical and cosmetic agents into cells, in particular specialized cells. As the new analogs are dephosphorylated by endogenous phosphorylases they will be transported into the cells where they are rephosphorylated and unable to pass out of the cell in phosphorylated form.
Toxic or cytopathic effects have not been observed with the analogs of this invention in a number of cell culture systems. It appears that the new analogs act as relatively untoxic polyspecific drugs with an amphoteric structure, as multiplex buffer molecules.
The new analogs have the general formula (Formula I)
wherein
R
1
is hydrogen, or acyl with 2-22 carbons (excluding retinoyl);
R
2
is hydrogen, or aryl with 6-30 carbons; provided that at least one of R
1
or R
2
is not hydrogen;
X
1
, X
2
and X
3
are independently O, S, or NR
3
;
R
3
is hydrogen, alkyl with 1-6 carbons, or acyl with 2-6 carbons;
Y is O, S, or NH;
Z is CH or N;
and include salts and common esters derived from unreacted remaining functional groups in Formula I. In a preferred embodiment X
1
is O, X
2
is NH, X
3
is S, Z is CH and Y is S.
The salts and common esters selected do not in a substantial way adversely affect the therapeutic, cosmetic, hygiene, anti-aging, cosmeceutical and nutritional functions of the new analogs.
Analogs in which R
1
is an &agr;-hydroxy acid such as glycolic or lactic or malic acid residue and their common salts and esters are preferred. Also preferred are analogs in which R
1
is derived from an FDA approved or accepted agent such as carminic acid and their common salts and esters. Carninic acid is a coloring agent approved by the FDA in foods and drugs. Also preferred are analogs in which R
1
is derived from an FDA approved or accepted agent, a vitamin such as pantothenic acid which analogs may function as Vitamin B
3
or B
5
delivering agents or ascorbic acid (Vitamin C) and their common salts and esters. Also preferred are analogs in which R
1
is derived from glucuronic acid or a glucuronic acid derivative such as hyaluronic acid with a molecular weight of 5×10
4
to 8×10
6
and their common salts and esters.
More preferred is a subgroup of analogs in which R
1
has the above meanings and R
2
is hydrogen and their common salts and esters.
Most preferred in this subgroup are analogs in which Z is CH, X
1
is oxygen, X
2
is NH, X
3
and Y are S, and their salts and common esters which do not in a substantial way adversely affect the therapeutic, cosmetic, hygiene, anti-aging, cosmeceutical and nutritional functions of the compounds in the subgroup.
Analogs in which R
2
is derived
Kesel Andreas J.
Oberthür Walter
Heller Ehrman White & McAuliffe LLP
Peselev Elli
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