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WO 2008/073257 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 19 June 2008 (19.06.2008) WO 2008/073257 Al (51) International Patent Classification: (74) Agent: GARRETT, Arthur S.; Finnegan, Henderson, A61K 31/195 (2006.01) A61P 43/00 (2006.01) Farabow, Garrett & Dunner, LLP, 901 New York Avenue, A61K 31/197 (2006.01) NW, Washington, District Of Columbia 20001-4413 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US2007/024944 kind of national protection available): AE, AG, AL, AM, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, (22) International Filing Date: CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, 6 December 2007 (06.12.2007) ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, (25) Filing Language: English LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, (26) Publication Language: English TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW (30) Priority Data: 60/873,561 8 December 2006 (08.12.2006) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant (for all designated States except US): XENO- GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, PORT, INC. [US/US]; 3410 Central Expressway, Santa ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), Clara, California 95051 (US). European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, (72) Inventors; and PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, (75) Inventors/Applicants (for US only): BARRETT, Ronald GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). W. [US/US]; 12900 Arroyo de Arguello, Saratoga, Califor nia 95070 (US). CUNDY, Kenneth C. [US/US]; 45 Sum Published: mit Ridge Place, Redwood City, California 94062 (US). — with international search report (54) Title: USE OF PRODRUGS OF GABA ANALOGS FOR TREATING DISEASES (57) Abstract: Methods of using prodrugs of GABA analogs and pharmaceutical compositions thereof to treat migraine, fibromyal- gia, amyotrophic lateral sclerosis, irritable bowel syndrome, social phobia, Parkinson's disease, asthma, cough, or chronic obstruc- tive pulmonary disease, and pharmaceutical compositions of prodrugs of GABA analogs useful in treating migraine, fibromyalgia, amyotrophic lateral sclerosis, irritable bowel syndrome, social phobia, Parkinson's disease, asthma, cough, or chronic obstructive pulmonary disease are disclosed. USE OF PRODRUGS OF GABA ANALOGS FOR TREATING DISEASES [001] This application claims the benefit under 35 U.S.C. § 119(e) of U.S. Provisional Application Serial No. 60/873,561 filed December 8, 2006, which is incorporated by reference herein in its entirety. Field [002] Methods and compositions disclosed herein relate to methods of using prodrugs of GABA analogs and pharmaceutical compositions thereof to treat migraine, fibromyalgia, amyotrophic lateral sclerosis, irritable bowel syndrome, social phobia, Parkinson's disease, asthma, cough, or chronic obstructive pulmonary disease in patients and to pharmaceutical compositions of prodrugs of GABA analogs useful in treating migraine, fibromyalgia, amyotrophic lateral sclerosis, irritable bowel syndrome, social phobia, Parkinson's disease, asthma, cough, or chronic obstructive pulmonary disease. Background [003] Migraine, fibromyalgia, irritable bowel syndrome, cough, asthma, and social phobia, are estimated to affect between 5% and 20% of the population. While less prevalent, amyotrophic lateral sclerosis and Parkinson's disease are significant neurodegenerative diseases. Chronic obstructive pulmonary disease is a major and increasing global health problem and is expected to become the third most common cause of death and the fifth most common cause of disability in the world by 2020. [004] The γ-aminobutyric acid (γ-aminobutyric acid is abbreviated herein as GABA) analog, gabapentin (1), has been approved in the United States for the treatment of epileptic seizures, diabetic neuropathy, post-herpetic neuralgia, and restless legs syndrome (Backonja et al, JAMA 1998, 280, 1831-36; Rose et al, Anaesthesia 2002, 57, 451-62). Pregabalin (2), another GABA analog, has been approved in the United States for the treatment of post-herpetic neuralgia. Gabapentin and/or pregabalin have also been shown or are proposed to be effective in treating a number of other medical disorders (Magnus, Epilepsia 1999, 40, S66-72) including migraine (see, e.g., Chronicle and Mulleners, Anticonvulsant drugs for migraine prophylaxis, The Cochrane Database of Systemic Reviews 2004, Issue 3; Mathew et al., Headache 2001, 41(2), 119-128; Mathew et al, Cephalalgia 1996, 16, 367; Wessely et al, Cephalalgia, 1987, 7, 477-78; Mathew, Headache 2001, Nov-Dec (Suppl), S18-S24; Di Trapani et al, Clin Ter 2000, 151, 145-148; and Capuano et al, Clin Ter 2004, 155(2-3), 79-87); fibromyalgia (see e.g., Nampiaparampil and Schmerling, Am J Manage Care 2004, 10, 794-800; Crofford, Curr Rheumatol Rep, 2004, 6, 274-80; Zareba, Drugs Today, 2005, 41(8), 509-516; and Dooley et al, U.S. Application Publication No. 2004/0180959), amyotrophic lateral sclerosis (see, e.g., Taylor, Rev Neurol, 1997 153(Suppl 1), S39-45; and Cory, Ann Pharmacother 1995, 29(11), 1160-61), irritable bowel syndrome (see, e.g., Taylor, Rev Neurol, 1997 153(Suppl 1), S39-45; and Cory, Ann Pharmacother 1995, 29(11), 1160-61), social phobia (see e.g., Pande et al., JClin Psychopharmacol 1999, 19, 341-348; and Pande et al, JClin Psychopharmacol 2000, 20(5), 544-546; Pande et al., JClin Psychopharmacol 2004, 24(2), 141-149; Selak, Curr Opin Investig Drugs 2001, 2(6), 828-834; Lauria-Horner and Pohl, Expert Opin Investig Drugs 2003, 12(4), 663-672; Kasper et al, Eur Neuropsychopharmacol 2002, 12 (Suppl), S341-S342; Rickels et al, 2002, Int J Neuropsychopharmacol 2002, 5, 14-15; and Smith et al, Eur Neuropsychopharmacol 2002, 12, S350), Parkinson's disease (see e.g., Olson et al, Am J. Med 1997, 102(1), 60-6; Faulkner et al, Ann Pharmacother 2003, 37(2), 282- 286; Marjama-Lyons and Koller, Drugs Aging 2000, 16(4), 273-278; and Van Blercom et al, CHn Neuropharmacol 2004, 27(3), 124-128), cough (Lee and Woo, Ann Oto Rhinol Laryngol 2005, 114(4), 253-7; Magistro, International Publication No. WO 00/67742; and Mintz and L , Am J Med 2006, 119, el3-el5), and pulmonary diseases such as asthma, bronchial conditions, and chronic obstructive pulmonary disease (Lomia, International Application No. WO 00/66096; Shrier and Taylor, EP 1192944; Magistro, WO 00/67742; and Bertrand et al, US 2004/0143014). [005] The broad pharmaceutical activities of GABA analogs such as gabapentin (1) and pregabalin (2): Gabapentin Pregabalin (1) (2) have stimulated intensive interest in preparing related compounds that have superior pharmaceutical properties in comparison to GABA, e.g., the ability to cross the blood- brain-barrier {see, e.g., Satzinger et al, U.S. Patent No. 4,024,175; Silverman et al, U.S. Patent No. 5,563,175; Horwell et al, U.S. Patent No. 6,020,370; Silverman et al, U.S. Patent No. 6,028,214; Horwell et al, U.S. Patent No. 6,103,932; Silverman et al, U.S. Patent No. 6,1 17,906; Silverman, International Publication No. WO 92/09560; Silverman et al, International Publication No. WO 93/23383; Horwell et al, International Publication No. WO 97/29101, Horwell et al, International Publication No. WO 97/33858; Horwell et al, International Publication No. WO 97/33859; Bryans et al, International Publication No. WO 98/17627; Guglietta et al, International Publication No. WO 99/08671; Bryans et al, International Publication No. WO 99/21824; Bryans et al, International Publication No. WO 99/3 1057; Belliotti et al, International Publication No. WO 99/31074; Bryans et al, International Publication No. WO 99/31075; Bryans et al, International Publication No. WO 99/61424; Bryans et al, International Publication No. WO 2000/1561 1; Belliot et al, International Publication No. WO 00/31020; Bryans et al, International Publication No. WO 00/50027; and Bryans et al, International Publication No. WO 02/00209). [006] One significant problem associated with the clinical use of many GABA analogs, including gabapentin and pregabalin, is rapid systemic clearance. Consequently, these drugs require frequent dosing to maintain a therapeutic or prophylactic concentration in the systemic circulation (Bryans et al. , Med. Res. Rev. 1999, 19, 149-177). For example, dosing regimens of 300-600 mg doses of gabapentin administered three times per day are typically used for anticonvulsive therapy. Higher doses ( 1800-3600 mg/day in three or four divided doses) are typically used for the treatment of neuropathic pain states. Doses of gabapentin up to 2400 mg/day with 300 mg administered eight times a day have been shown to be effective in treating migraine {see, e.g., Mathew et al, Headache 2001, 41, 119-128; Mathew, Cephalalgia 1996, 16, 367; Magnus-Miller et al, American Pain Society Program, 17th Annual Meeting, Abstract No. 645, San Diego, CA, November 5- 8,1998; Wessely et al., Cephalalgia 1987, 7(Suppl 6), 411-41%; Di Trapani et al, Clin Ter 2000, 151, 145-148; and Capuano et al, Clin Ter 2004, 155(2-3), 79-87). Although oral sustained released formulations are conventionally used to reduce the dosing frequency of drugs that exhibit rapid systemic clearance, oral sustained release formulations of gabapentin and pregabalin have not been developed because these drugs are not absorbed via the large intestine.
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