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(12) United States Patent (10) Patent No.: US 8,003,688 B2 Frimman Berg (45) Date of Patent: Aug

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(12) United States Patent (10) Patent No.: US 8,003,688 B2 Frimman Berg (45) Date of Patent: Aug US008.003688B2 (12) United States Patent (10) Patent No.: US 8,003,688 B2 Frimman Berg (45) Date of Patent: Aug. 23, 2011 (54) METHOD OF TREATING SYMPTOMS OF (56) References Cited COMMON COLD, ALLERGIC RHINITIS AND NFECTIONS RELATING TO THE U.S. PATENT DOCUMENTS RESPRATORY TRACT 3.420,815 A 1/1969 Courbat 3,516,984 A 6, 1970 Courbat 4,888,326 A 12/1989 Horrobin (75) Inventor: Kurt Frimman Berg, Charlottenlund 4.956,385 A 9/1990 Eby, III (DK) 5,096,887 A 3/1992 Casley-Smith 5,834,000 A 1 1/1998 Yng-Wong (73) Assignee: ImmuPharm Aps, Aalborge (DK) 5,888,527 A 3, 1999 Nashimoto et al. 5,922,756 A 7, 1999 Chan (*) Notice: Subject to any disclaimer, the term of this 5,935,996 A 8/1999 Yamaguchi patent is extended or adjusted under 35 6,224,872 B1 5/2001 Shibuya et al. U.S.C. 154(b) by 1336 days. FOREIGN PATENT DOCUMENTS DE 3603227 8, 1987 (21) Appl. No.: 11/172,878 DE 1994.95.75 4/2001 EP O2O4987 12, 1986 EP O396.251 11, 1990 (22) Filed: Jul. 5, 2005 EP O417385 3, 1991 (65) Prior Publication Data (Continued) US 2005/0245467 A1 Nov. 3, 2005 OTHER PUBLICATIONS van Acker et al., Cancer Research, 1993:53(19):4603-4607 Related U.S. Application Data (abstract.* (63) Continuation of application No. 10/363.430, filed as (Continued) application No. PCT/DK01/00515 on Jul. 23, 2001, now Pat. No. 7,166,640. Primary Examiner — San-Ming Hui (74) Attorney, Agent, or Firm — Iver P. Cooper (30) Foreign Application Priority Data (57) ABSTRACT Jul. 28, 2000 (DK) ................................. 2OOOO1152 The present invention relates to methods of treating condi Sep. 4, 2000 (DK)...... ... 2000 O1316 tions and/or symptoms related to common cold of the upper Dec. 23, 2000 (DK)...... ... 2000 O1935 and/or lower respiratory tract and/or eyes. In particular the Jan. 3, 2001 (DK) ................................. 2001 OOOO7 invention relates to the methods of treating conditions and/or May 22, 2001 (DK) ................................. 2001 OO827 symptoms related to common cold comprising administra tion of a flavonoid or administration of a flavonoid in combi (51) Int. Cl. nation with a metal. The invention furthermore describes AOIN 43/16 (2006.01) compositions comprising a metal and a flavonoid useful for (52) U.S. Cl. ....................................................... 514/.456 the treatment of conditions and/or symptoms relates to com (58) Field of Classification Search ................... 5147456 mon cold. See application file for complete search history. 14 Claims, 7 Drawing Sheets SC -- symbomo -a-symptom -- sympton2 --8- symptom3 -- symptom 4 Dayo: the status of the patient at the first visit at the doctor. Day 1:24 h after the 1st visit Day 2:48 h after the 1st visit Day 3:72 h after theist. visit US 8,003,688 B2 Page 2 FOREIGN PATENT DOCUMENTS K. Parfitt, Matindale The complete drug reference . pp. 1373 1374. EP O754450 1, 1997 EP O861.662 9, 1998 Tej N. Kaul, Elliot Middleton Jr., Pearay L. Ogra. Antiviral effect of JP O4368331 12/1992 flavonoids on human viruses, Journal of Medical Virology 15:71-79. JP O82393.19 9, 1996 1985. JP O9056333 3, 1997 S. B. Mossad, M. L. Macknin, S. V. Medendorph, P. Mason, Zinc JP O9227373 9, 1997 gluconate lozenges for treating the common cold, Annals of internal JP 10257856 9, 1998 medicine vol. 125, p. 81-88, 1996. JP 1110O325 4f1999 I.M. Selivanova, N.A. Tyukavkina, Yu.A. Kolesnik, V.K. Kolkhir, JP 10110785 11, 1999 VLyubimov, Investigation of absorption of diguertin in vitro JP 11302184 11, 1999 gastrointestinal model, Farmatsiya, 47:27-28, 1998. JP 2OOO327573 11, 2000 M. Tordea, M. L. Ferrándiz, M. J. Alcaraz, Influence of anti-inflam WO WO 88,03800 6, 1988 matory flavonoids on degranulation and arachidonic acid release in WO WO 88,03805 6, 1988 rat neutrophils, Z. Naturforsch, vol. 49, p. 235-240, 1993. WO WO 97.27 177 7/1997 Abisheganaden, et al., “Effect of Clarithromycin on Experimental WO WO 98.30228 7, 1998 WO WO 98.47534 10, 1998 Rhinovirus-16 Colds: A Randomized, Double-Blind, Controlled WO WO99,07381 2, 1999 Trial”. The American Journal of Medicine, vol. 108, pp. 453-459, WO WO99,163.19 4f1999 Apr. 15, 2000. WO WOOOf 70949 11, 2000 Berg, et al., "Zinc Potentiates the Antiviral Action of Human IFN-O. WO WOO1,03681 1, 2001 Tenfold'. Journal of Interferon and Cytokine Research, vol. 21, pp. WO WOO1? 49.285 T 2001 471-474, 2001. WO O2O76422 10, 2002 Black, P.N., “Anti-inflammatory effects of macrollide antibiotics'. Eur: Respir.J., vol. 10, pp. 971-972, 1997. OTHER PUBLICATIONS Bardsley-Elliot, et al., "Oseltamivir. Drugs, vol. 58(5), pp. 851-860, Nov. 1999. Powell, Journal of Nutrition, 2000: 130(5):1447S-1454S.* Farr, et al., “A Randomized Controlled Trial of Glucoccorticoid Pro Kang. Experimental Biology and Medicine, 1999:222(3):263-273.* phylaxis against Experimental Rhinovirus Infection”. J. Infect. Dis., Baumann, et al., “Flavonoids and Related. Compounds as Inhibitors vol. 162, pp. 1173-1177, Nov. 1990. of Arachidonic Acid Peroxidation”. Prostaglandins, Jul. 1980. Geist, et al., “In Vitro Activity of Zinc Salts against Human “The Merck Manual of Diagnosis and Therapy'. Merck Research Rhinoviruses'. Antimicrobial Agents and Chemotherapy, vol. 31. Laboratories, Seventeenth Edition, Whitehouse Station, N.J., pp. No. 4, pp. 622-624. Apr. 1987. 556-569, chapter 68, section 6, 1999. Jackson, et al., "Zinc and the Common Cold: A Meta-Analysis M. H. Beers, M. d. berkow, The Merch manual of diagnosis and Revisted”. J. Nutri, vol. 130, pp. 1512s-1515s, 2000. therapy, p. 1277-1293, 1999 Merck Research. Lorber, BennettMD, “The Common Cold” Journal of General Inter J. V. Formica, W. Regelson, Review of the biology of quercetin and nal Medicine, vol. 11, pp. 229-236, Apr. 1996. related bioflavonoids. Fol Chem. Toxic. vol. 33, No. 12, pp. 1061 Rink, et al., "Zinc-Altered Immune Function and Cytokine Produc 1080, 1995. tion”. J. Nutri, vol. 130, pp. 1407S-1411S, 2000. J. E. F. Reynolds, Martindale—The extra phamacopoeia, thirty-first edition, pp. 1679-1680, 1996. * cited by examiner U.S. Patent Aug. 23, 2011 Sheet 1 of 7 US 8,003,688 B2 -O- symborn 0 - A- symptom 1 -v- symptom 2 --8- symptom 3 ---- symptom 4 Day 0: the status of the patient at the first visit at the doctor. Day 1:24 h after the 1st visit Day 2: 48 h after the 1st visit Day 3: 72 h after the 1st visit Fig. 1 U.S. Patent Aug. 23, 2011 Sheet 2 of 7 US 8,003,688 B2 Malaise Scores From Treated vs. Non-Treated Patients 3.0 2.5 2.0 -- non-treated patient) f 5 1.0 0.5 treated patients O.0 O 1 2 3. 4 days of treatment day 0 : 1s. visit - treatment initiated day 1: 24 h treatment day 2: 48 h treatment day 3: 48 h treatment ) data taken from Figure 4 (day 2 is used as day O in this study) in Jackson et al...Arch. internal Med. 101; 267-278, 1958 Fig. 2 U.S. Patent Aug. 23, 2011 Sheet 3 of 7 US 8,003,688 B2 Sore Throat Scores of Treated Patients vs. Non-treated 3 -- non-treated patients ) treated patients O 1 2 3 4 days of treatment day 0 : 1st, visit - treatment initiated day 1: 24 h treament day 2: 48 h treatment day 3: 48 h treatment Fig. 3 U.S. Patent Aug. 23, 2011 Sheet 4 of 7 US 8,003,688 B2 Sneezing Scores From Treated vs. Non-Treated Patients 3.00 2.75 2.50 2.25 2.00 1.75 150 1.OO 0.75 -- non-treated patient) O.50 0.25 treated patients O.OO O 1. 2 3 4 days of treatment day 0 : 1st visit - treatment initiated day 1: 24 h treatment day 2:48 h treatment day 3: 48 h treatinent Fig. 4 U.S. Patent Aug. 23, 2011 Sheet 5 of 7 US 8,003,688 B2 %-Reduction in Mean Total Symptom Score per Patient Between The N.H. and KB Trials 60 50 -O-96reduction KB 4 O - A - %reduction Hertz 3 O 2 O 10 day U.S. Patent Aug. 23, 2011 Sheet 6 of 7 US 8,003.688 B2 Total Symptom score per common cold patient (7 patients)") all treated with Immulwaxzn 2O.O 17.5 15.O 12.5 10.0 7.5 5.0 2.5 O.O 0.0. O.5 10 15 2.0 2.5 3.0 3.5 days of treatment Fig. 6 U.S. Patent Aug. 23, 2011 Sheet 7 of 7 US 8,003,688 B2 1.1 O 0.9 -- Cell control(-fFN) 0.8 0.7 s 0.6 0.5 0.4 0.3 C ZnCluc. (0.2mM) P 7 AN C 0.2d M T ---. ------(p-------------e -: --O-- ZnCluc.(0.07mv) 0.1 is -i :- 0.0 0.00 0.25 O.50 O.75 100 1.25 150 1.75 interferon units/m Fig. 7 US 8,003,688 B2 1. 2 METHOD OF TREATING SYMPTOMS OF up to 70-75% of all patients suffering from common colds COMMON COLD, ALLERGIC RHINITIS AND have a rhinovirus infections ongoing either as a single infec NFECTIONS RELATING TO THE tion or co-infection (Spector, 1995). RESPRATORY TRACT It has been estimated that the average pre-school child experiences 6-10 upper respiratory infections or common This is a continuation of Ser. No.
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