Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Halogenated hydrocarbon doai
Reexamination Certificate
2000-05-25
2001-09-18
Jarvis, William R. A. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Halogenated hydrocarbon doai
Reexamination Certificate
active
06291534
ABSTRACT:
TECHNICAL FIELD
My invention relates to the field of molecules with two aromatic condensed rings (naphtalenic rings) characterized by a good activity against inflammation through inhibitory actions in one or more passages of the “fall” of the arachidonic acid.
BACKGROUND ART
From the beginning of the nineties in the medical literature lots of studies appeared about a molecule patented as lonapalene (drawings,
FIG. 1
) with a great power against inflammation of the skin Lonapalene (6-chloro-2,3-dimethoxynaphthalendioldiacetate) has a statistically significant reduction in the levels of material similar or identical to the chemoattractant arachidonate 5-lipoxygenase product, leukotriene B4 (Black A. K., LAMP R D., Malled A T., Cunningham F M., Hofbauer M., Greaves M W.; PHARMACOLOGIC AND CLINICAL EFFECTS OF LONAPALENE-RS43-179-A 5-LIPOXYGENASE INHIBITOR IN PSORIASIS; JOURNAL OF INVESTIGATIVE DERMATOLOGY 95(1):50-4, 1990 July) A wide variety of agents have been reported as 5-lipooxygenase inhibitors. The majority of the series appear to be lipophilic reducing agents, including phenols, partially saturated.
Aromatics and compounds containing heteroatom-hetero atom bonds are the-same. Many of these are not selective 5-LO inhibitors.
In vivo sistemic activity for many of these has been in general, disappointing, probably because of poor bioavailability caused by lipophilicity and metabolic instability (oxidation and conjugation of phenolic compounds). However, topically a number of agents have shown promise for skin inflammation, and best of all, lonapalene; (Batt D G., 5-LIPOXYGENASE INHIBITORS AND THEIR ANTI-INFLAMMATORY ACTIVITIES, PROGRESS IN MEDICINAL CHEMISTRY, 29:1-63, 1992).
Unfortunately, the clinical utilisation of lonapalene wasn't successful, probably because of the remarkable side effects. Lots of attempts have been made to find other topical nonsteroidal antipsoriatic agents analogues of lonapalene, without any success;(Venuti M C., Loe B E., Jones G H., Young G M., TOPICAL NONSTEROIDAL AN TIPSORIATIC AGENTS. 2.2,3-ALKYLIDENEDIOXYNAPHTALENE ANA LOGUES OF LONAPALENE, JOURNAL OF MEDICINAL CHEMISTRY, 31(11):2132-6, 1988 November). (Jones G H., Venuti M C., YOUNG J M., Murthy D V., Loe B E., Simpson R A., Berks A H., Spires D A., Malonej P J., Kruseman M., et al., TOPICAL NON STEROIDAL ANTIPSORIATIC AGENTS. 1.1,2,3,4,-TETRAOXYGENATED NAPHTALENE DERIVATIVES, JOURNAL OF MEDICINAL CHEMISTRY, 29(8):1504-11, 1986 August).
DISCLOSURE OF INVENTION
Considering what I reported before, my attention turned to find out a molecule as efficacious as lonapalene avoiding the negative side effects.
After a first screening which led me to select molecules without halogens, a molecule has been found:
2,6 or 2,7-dimethoxynaphtalene that I patented with the name of ENDIPALENE.
Endipalene seems to have the same action mechanism of lonapalene excluding remarkable side effects.
REFERENCES:
patent: 5712312 (1998-01-01), Langlois et al.
patent: 6156790 (2000-12-01), Posner et al.
patent: 6160004 (2000-12-01), Posner et al.
N. Motoyama et al., Pesticide Biochemistry and Physiology, vol. 9 (1978), pp. 255-262; “Endogenous Inhibitors of Glutathione S-Transferase in House Flies”.
D. G. Batt, Progress in Medicinal Chemistry, vol. 29 (1992), pp. 1-63; “5-Lipoxygenase Inhibitors and their Anti-inflammatory Activities”.
A. K. Black et al., J. of Investigative Dermatology, vol. 95, No. 1, Jul. 1990, pp. 50-54; “Pharmacologic and Clinical Effects of Lonapalene (RS 43179), a 5-Lipoxygenase Inhibitor, in Psoriasis”.
G. H. Jones et al., J. Med. Chem., vol. 29, No. 8 (1986), pp. 1504-1511; “Topical Nonsteroidal Antipsoriatic Agents. 1. 1,2,3,4-Tetraoxygenated Naphthalene Derivatives”.
P. A. Lehman, Pharmaceutical Research, vol. 9, No. 9 (1992), pp. 1145-1151; “Percutaneous Absorption and Metabolism of Lonapalene in Psoriatic Skin”.
M. C. Venuti et al., J. Med. Chem., vol. 31, No. 11 (1988), pp. 2132-2136; “Topical Nonsteroidal Antipsoriatic Agents. 2. 2,3,-(Alkylidenedioxy)naphthalene Analogues of Lonapalene”.
Arent Fox Kintner & Plotkin & Kahn, PLLC
Jarvis William R. A.
Kim Vickie
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