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Indole Alkaloids Useful As Anti-Inflammatory Agents

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Indole Alkaloids Useful As Anti-Inflammatory Agents Europäisches Patentamt *EP000776204B1* (19) European Patent Office Office européen des brevets (11) EP 0 776 204 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 31/40, C07D 209/94, of the grant of the patent: A61P 29/00 27.11.2002 Bulletin 2002/48 (86) International application number: (21) Application number: 95928352.4 PCT/US95/10052 (22) Date of filing: 08.08.1995 (87) International publication number: WO 96/006607 (07.03.1996 Gazette 1996/11) (54) INDOLE ALKALOIDS USEFUL AS ANTI-INFLAMMATORY AGENTS INDOLALKALOIDE ALS ANTIENTZÜNDLICHE WIRKSTOFFE ALCALOIDES RENFERMANT DE L’INDOLE UTILES EN TANT QU ’AGENTS ANTI-INFLAMMATOIRES (84) Designated Contracting States: • GRACE, Krista J.S. AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL Goleta, CA 93117 (US) PT SE • PROTEAU, Philip J. Murray, UT 84107 (US) (30) Priority: 29.08.1994 US 297022 • ROSSI, James Corvallis, OR 97333 (US) (43) Date of publication of application: 04.06.1997 Bulletin 1997/23 (74) Representative: Goldin, Douglas Michael et al J.A. KEMP & CO. (73) Proprietor: The Regents of the University of 14 South Square California Gray’s Inn Oakland, CA 94607-5200 (US) London WC1R 5JJ (GB) (72) Inventors: (56) References cited: • GERWICK, William H. • G.L. HELMS ET AL.: "Scytonemin A, a novel Corvallis, OR 97330 (US) calcium antagonist from a blue-green alga" J. • JACOBS, Robert S. ORGANIC CHEMISTRY, vol. 53, no. 6, 1988, Santa Barbara, CA 93101 (US) pages 1298-1307, XP002063613 • CASTENHOLZ, Richard • EXPERIENTIA, Volume 49, issued 1993, Elmira, OR 97437 (US) PROTEAU et al., "The Structure of Scytonemin, • GARCIA-PICHEL, Ferran an Ultraviolet Sunscreen Pigment from Sheaths 28359 Bremen (DE) of Cyanobacteria", pages 825-829. Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 776 204 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 776 204 B1 Description BACKGROUND OF THE INVENTION 5 1. Field Of The Invention [0001] The present invention relates generally to compounds which have more than one pharmaceutically desirable activity. More particularly, the present invention is directed to a newly isolated indole alkaloid compound and analogs thereof which have been found to be effective anti-inflammatory agents while also being useful as ultraviolet radiation 10 absorbers, i.e. UV protective agents. 2. Description of Related Art [0002] A yellow-green pigment was first isolated from sheathed cyanobacteria in the late 1870's. Although the pig- 15 ment included a complex mixture of unidentified compounds, the single term "scytonemin" was introduced to identify the pigment. Since its initial discovery, scytonemin has been isolated and identified in more than 30 species of sheathed cyanobacteria. These sheathed bacteria which contain scytonemin have been found in diverse geographic regions wherever exposure to strong solar irradiance occurs. These regions have included freshwater, terrestrial and marine habitats. 20 [0003] An important characteristic of the scytonemin pigment is its ability to absorb ultra-violet (UV) radiation. Sheathed cyanobacteria or similar ancestral forms occur commonly as microfossils in strata of biogenic origin from the Proterozoic period and even earlier. Since UV fluxes were considerably higher then than now, it is likely that de- velopment of scytonemin for its UV-screening properties was important to the evolution of cyanobacteria. The scytone- min pigment absorbs most strongly in the UV-A spectral region. There is also significant absorbance in the UV-B region. 25 [0004] Although scytonemin pigment has been known as a UV absorber for many years, the various complex group or groups of compounds which are present in the pigment have not been completely isolated or identified. Accordingly, the specific ingredient or ingredients in scytonemin pigment which provide it with such strong UV absorbing properties have remained unknown. [0005] Proteau et al, Experientia, volume 49, 825-829 (1993) describes the structure of scytonemin and its reduction 30 product, and reports that scytonemin has been shown to provide significant protection to cyano bacteria against damage by ultraviolet radiation. [0006] J. Organic Chemistry, volume 53(6), t 298-1307, 1988 describes calcium antagonist activity associated with scytonemin. 35 SUMMARY OF THE INVENTION [0007] In accordance with the present invention, it was discovered that one of the compounds present in scytonemin pigment is an indole alkaloid which not only is a strong UV absorber, but also exhibits strong activity as an anti-inflam- mation agent. The purified indole alkaloid, along with synthetically derived analogs, may be used alone or in combination 40 with a pharmaceutically acceptable carrier to treat inflammation while at the same time providing UV protection. [0008] Indole alkaloid compounds in accordance with the present invention have the formula 45 50 55 where R and R' are H, an alkyl group having up to 5 carbon atoms or -CO-(CH2)n-CH3 where n=0to16.Thecompound where R and R' are H may be isolated and purified from naturally occurring scytonemin pigment. Ether analogs where R and R' are alkyl groups having up to 5 carbon atoms may be prepared from the naturally occurring dihydroxy indole alkaloid compound using conventional synthetic pathways. The diacetate analogs may also be prepared using well- 2 EP 0 776 204 B1 known pathways for preparing acetate analogs from the naturally occurring dihydroxy indole alkaloid compound. [0009] The indole alkaloid compounds in accordance with the present invention are effective anti-inflammation agents which demonstrate high anti-inflammatory activity when subjected to standard anti-inflammatory test protocols. These indole alkaloids also exhibit strong UV absorption. As a result, the compounds of the present invention may advanta- 5 geously be used to treat skin inflammation while at the same time functioning as a UV protective agent. [0010] The above discussed and many other attendant features of the present invention will become better under- stood by reference to the following detailed description. DETAILED DESCRIPTION OF THE INVENTION 10 [0011] The indole alkaloid compounds in accordance with the present invention have the formula 15 20 25 where R and R' are H, an alkyl group having up to 5 carbon atoms or -CO-(CH2)n-CH3 where n=0to16.Thepresent invention also covers the reduced form of this compound which has the formula 30 35 40 where R and R' are H, an alkyl group having up to 5 carbon atoms or -CO-(CH2)n-CH3 where n = 0 to 16. [0012] The compound of the present invention where R and R' are both H (Compound 1) can be isolated and purified from naturally occurring scytonemin pigment using conventional separation and purification procedures. The isolation and characterization of Compound 1 is set forth in P.J. Proteau et al., "The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria," Experientia 49 (1993), pages 825 to 829. 45 [0013] Once having obtained the Compound 1, the ether and diacetate analogs as defined in the above formula may be prepared according to conventional procedures for forming diether and diacetate derivatives. Acetylation was ac- complished generally following the procedure detailed in Gerwick, W.H. and Fenical, W., "Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (lamouroux) Papenfuss," J. Org. Chem. 1981, 46, 22-27, except that the reaction was quenched with MeOH and the excess reagents and solvents were removed in vacuo. 50 [0014] Metylation was accomplished generally following the method of Stoochnoff, B.A. and Benoiton, N.L., "The methylation of some phenols and alcohols with sodium hydride/methyl iodide in tetrahydrofuran at room temperature," Tetrahedron Lett. 1973, 21-24, except that anhydrous K2CO3 (potassium carbonate) was used instead of sodium hy- dride as the base. [0015] Preferred exemplary compounds are the dimethyl ether where R and R' are methyl (Compound 2) and the 55 diacetate where R and R' are -CO-(CH2)n-CH3 and n = 0 (Compound 3). In addition, if desired, additional analogs may be prepared wherein one or more halogen groups are substituted on the phenyl rings adjacent to the -OR or OR' groups. [0016] The indole alkaloid compounds in accordance with the present invention are useful for treating inflammation. The compounds may be used in the same manner as conventional anti-inflammatory agents indomethacin, hydrocor- 3 EP 0 776 204 B1 tisone, naprocin and other non-steroidal anti-inflammatory agents. The compounds are effective for both topical appli- cation and in vivo use. When used for topical application, the compounds function both as a UV protective agent and anti-inflammation agent. [0017] Pharmaceutical compositions which contain the indole alkaloids in accordance with the present invention are 5 useful in the treatment of rheumatoid arthritis, osteoarthritis, rheumatic carditis, collagen and/or auto-immune diseases such as myasthenia gravis, allergic diseases, bronchial asthma and ocular and skin inflammatory diseases such as poison ivy. The compositions are also useful in treating proliferative diseases such as psoriasis. [0018] The compositions are also useful as adjuvant therapy associated with organ and tissue transplants and any neurological disease involving metabolism of nervous tissue phospholipid such as multiple sclerosis. The compositions 10 may also be used to treat secondary inflammation resulting from septic shock and reprefusion injury associated with coronary by-pass surgery and other intra arterial surgical procedures. Because of their selective antagonism of chem- ical irritation (i.e., PMA inflammation) the compounds can be useful in the treatment of insect bites, bee, wasp stings, snake bites or any venom in which a major constituent is the enzyme phospholipase A2.
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