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(12) United States Patent (10) Patent No.: US 6,623,730 B1 Williams Et Al

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(12) United States Patent (10) Patent No.: US 6,623,730 B1 Williams Et Al USOO662373OB1 (12) United States Patent (10) Patent No.: US 6,623,730 B1 Williams et al. (45) Date of Patent: Sep. 23, 2003 (54) THERAPEUTIC USES OF POLYMERS AND Byrom, “Miscellaneous Biomaterials,” in Biomaterials (D. OLGOMERS COMPRISING Byrom, ed.) pp. 333-359 (MacMillan Publishers, London GAMMA-HYDROXYBUTYRATE 1991). Colombo, et al., “Involvement of GABA(A) and GABA(B) (75) Inventors: Simon F. Williams, Sherborn, MA receptors in the mediation of discriminative Stimulus effects (US); David P. Martin, Arlington, MA of gamma-hydroxybutyric acid.” Physiology & Behavior (US) 64:293–302 (1998). Dubois, et al., “Macromolecular Engineering of Polylac (73) Assignees: Tepha, Inc., Cambridge, MA (US); tones and Polylactides. 12. Study of the Depolymerization Metabolix, Inc., Cambridge, MA (US) Reactions of Poly (e-caprolactone) with Functional Alumi (*) Notice: Subject to any disclaimer, the term of this num Alkoxide End Groups.” Macromolecules 26:4407-12 patent is extended or adjusted under 35 (1993). U.S.C. 154(b) by 99 days. Entholzner, et al., “EEG changes during Sedation with gamma-hydroxybutyric acid.” Anaesthesist 44:345-350 (21) Appl. No.: 09/661,948 (1995). Gerra, et al., “Flumazenil effects on growth hormone (22) Filed: Sep. 14, 2000 response to gamma-hydroxybutyric acid.” International Related U.S. Application Data Clinical Psychopharmacology 9:211-215 (1994). (60) Provisional application No. 60/182,371, filed on Feb. 14, Gross, et al., “Polymerization if B-monosubstituted-b-pro 2000, and provisional application No. 60/153.844, filed on piolactones using trialkylaminimum-water catalytic SyS Sep. 14, 1999. tems and polymer characterization,” Macromolecules 21:2657–2668 (1988). (51) Int. Cl." ........................ A61K 31/765; A61 K9/20; Hocking & Marchessault, “Syndiotactic poly(R, A61K 9/70; A61K 13/00; CO7C 69/66 S)-B-hydroxybutyrate isolated from methyaluminoxane catalyzed polymerization.” Polym. Bull. 30:163–170 (1993). (52) U.S. Cl. .................... 424/78.37; 424/464; 424/449; Hocking & Marchessault, “Biopolyesters” Griffin, Ed., 424/422; 560/185 “Chemistry and Technology of Biodegradable Polymers,” pp. 48-96 (Chapman and Hall, London, 1994). (58) Field of Search .............................. 424/78.37, 464, Holmes, “Biologically Produced (R)-3-hydroxyalkanoate 424/451, 449, 422, 514/533,923, 962, Polymers and Copolymers,” in Bassett Ed., “Developments 2,557; 560/185 in Crystalline Polymers,” pp. 1-65 (Elsevier, London, vol. 2, (56) References Cited 1988). Hori, et al., “Ring-Opening Copolymerization of Optically U.S. PATENT DOCUMENTS Active B-Butyrolactone with Several Lactones Catalyzed by 5,563,239 A 10/1996 Hubbs et al. Distannoxane Complexes: Synthesis of New Biodegradable 5,753,708 A 5/1998 Koehler et al. Polyesters,” Macromolecules 26:4388-4390 (1993). 5,840,331 A * 11/1998 Van Cauter et al. ........ 424/464 5.990,162 A 11/1999 Scharf ........................ 514/533 (List continued on next page.) FOREIGN PATENT DOCUMENTS Primary Examiner Thurman K. Page Assistant Examiner Blessing Fubara EP O 429 403 A2 5/1991 (74) Attorney, Agent, or Firm-Holland & Knight LLP EP O 344. 704 A1 12/1991 WO WO 97/15681 A1 5/1997 (57) ABSTRACT WO WO 97/30042 A1 8/1997 WO WO 99/14313 A2 3/1999 Oligomers and polymer compositions are provided which WO WO 99/32536 A1 7/1999 comprise GHB and produce GHB after administration in WO WO 99/35192 A1 7/1999 Vivo. Devices for the Storage and delivery of these polymers WO WO 99/35.192 * 7/1999 and oligomers are also provided. These oligomers and polymer compositions are useful in a variety of applications. OTHER PUBLICATIONS The compositions can be used therapeutically, for example, Abate, et al., “Separation and Structural characterizations of in the treatment of patients with narcolepsy, chronic cyclic and open chain oligomers produced in the partial Schizophrenia, catatonic Schizophrenia, atypical psychoses, pyrolysis of microbial poly(hydroxyutyrates).” Macromol chronic brain Syndrome, neurosis, alcoholism, drug addic ecules 28(23):7911–1916 (1995). tion and withdrawal, Parkinson's disease and other neurop Addolorato, et al., “Maintaining abstinence from alcohol harmacological illnesses, hypertension, ischemia, circula with gamma-hydroxybutyric acid.” The Lancet 351:38 tory collapse, radiation exposure, cancer, and myocardial (1998). infarction. Other uses for the compositions include anesthe Agostini, et al., “Synthesis and Characterization of sia induction, Sedation, growth hormone production, height Poly-8-Hydroxybutyrate. I. Synthesis of Crystalline DL ened Sexual desire, anorectic effects, euphoria, Smooth Poly-8-Hydroxybutyrate from DL- B-Butyrolactone.” muscle relaxation, muscle mass production, and Sleep, Polym. Sci. Part A-1, 9:2775-2787 (1971). including rapid eye movement Sleep. In a still further Andriamampandry, et al., “Cloning of a rat brain Succinic embodiment, the oligomers and polymerS may be used to semialdehyde reductase involved in the synthesis of the produce absence Seizures. neuromodulator Y-hydroxybutyrate,” Biochem. J. 334:43–50 (1998). 29 Claims, No Drawings US 6,623,730 B1 Page 2 OTHER PUBLICATIONS Ropero-Miller & Goldberger, “Recreational drugs. Current Hori, et al., “Ring-Opening Polymerization of Optically trends in the 90s,” Clinics in Laboratory Medicine, Active B-Butyrolactone Using Distannoxane Catalysts: 18:727-746 (1998). Synthesis of High Molecular Wright Saito, et al., “Microbial Synthesis and properties of Poly(3-hydroxybutyrate).” Macromolecules 26:5533–5534 Poly(3-hydroxybutyrate-co-4-hydroxybutyrate).” Polymer (1993). International 39:169–174 (1996). Horowitz, et al., Macromolecules 32:3347–3352 (1999). Scharf, et al., “Pharmacokinetics of gammahydroxybutyrate Kaufman & Nelson, “An overview of gamma-hydroxybu (GHB) in narcoleptic patients.” Sleep 21:507–514 (1998). tyrate catabolism: the role of the cytosolic NADP(+)-de Sendelbeck & Girdis, “Disposition of a 14C-labeled bio pendent oxidoreductase EC 1.1.1.19 and of a mitochondrial erodible polyorthoester and its hydrolysis products, hydroxyacid-oxoacid transhydrogenase in the initial, rate 4-hydroxybutyrate and cis,trans-1,4-bis(hydroxymethyl) limiting step in this pathway,” Neurochemical Research cyclohexane, in rats,” Drug Metabolism & Disposition 16:965–974 (1991). 13:291-295 (1985). Kemnitzer, et al., “Preparation of predominantly Syndiotac Snead, “The gamma-hydroxybutyrate model of absence tic Poly(B-hydroxybutyrate) by the Tributylin Methoxide Seizures: correlation of regional brain levels of gamma-hy Catalyzed Ring-Opening Polymerization of racemic droxybutyric acid and gamma-butyrolactone with Spike R-Butyrolactone,” Macromolecules 26:1221–1229 (1993). wave discharges.” Neuropharmacology 30:161-167 (1991). KleinSchmidt, et al., “Continuous Sedation during Spinal Song, et al., Biotechnol. Lett. 21:193–197 (1999). anaesthesia: gamma-hydroxybutyrate VS. propofol, Euro Steinbichel, “Polyhydroxyalkanoic Acids,” in Byrom Ed., pean Journal of Anaesthesiology 16:23–30 (1999). “Biomaterials' MacMillan Publishers, London, 1991, pp. KleinSchmidt, et al., “Total intravenous anaesthesia using 123-213 propofol, gamma-hydroxybutyrate or midazolam in combi Tanahashi & Doi, “Thermal Properties and Stereoregularity nation with Sufentanil for patients undergoing coronary of Poly(3-hydroxybutyrate) Prepared from optically Active artery bypass Surgery, European Journal Of Anesthesiology B-Butyrolactone with a Zinc-Based Catalyst,” Macromol 14:590–599 (1997). Lafferty et al., “Microbial Production of ecules 24:5732-5733 (1991). Poly-8-hydroxybutyric acid,” Rehm and Reed, Eds., “Bio Tanaka, et al., "Clinical application of 4-hydroxybutyrate technology” Verlagsgesellschaft, Weinheim, vol. 66, 1988, Sodium and 4-butyrolactone in neuropsychiatric patients,” pp. 135–176. Folia Psychiatrica et Neurologica 20:9–17 (1966). Le Borgne & Spassky, "Stereoelective polymerization of Tunnicliff, "Sites of action of gamma-hydroxybutyrate f-butyrolactone,” Polymer 30:2312–2319 (1989). (GHB)--a neuroactive drug with abuse potential,” Clincial Lebedev & Yevstropov, Makromol. Chem. 185:1235–1253 Toxicology 35:581–590 (1997). (1984). Williams & Peoples, “Biodegradable plastics from plants,” Madison & Huisman, “Metabolic engineering of CHEMTECH 26:38–44 (1996). poly(3-hydroxyalkanoates): from DNA to plastic,” Micro Williams & Peoples, “Making Plastics Green,” Chem. Br. biol. Mol. Biol. Rey: 63–21–53 (1999). 33:29-32 (1997). Miller & Seebach, “Poly(hydroxyalkanoates): A Fifth Class Williams, et al., “PHA applications: addressing the price of Physiologically Important Organic Biopolymers,” Angew performance issue I. Tissue engineering.” Int. J. Biol. Mac Chem. Int. Ed. Engl. 32:477–502 (1993). romol. 25:111-121 (1999). Nelson, et al., “The extraneural distribution of gamma-hy Xie, et al., “Ring-opening Polymerization of B-butyrolac droxybutyrate,” J. Neurochem. 37:1345-1348 (1981). tone by Thermophilic Lipases,” Macromolecules Reynolds, Martindale. The Extra Pharmacopeia, p. 1264, 30:6997–6998 (1997). (Thirty First Edition, Royal Pharmaceutical Society, Lon don, 1997). * cited by examiner US 6,623,730 B1 1 2 THERAPEUTIC USES OF POLYMERS AND plasma levels of growth hormone after injection in healthy OLIGOMERS COMPRISING GAMMA subjects (Gerra, et al., Int'l Clinical Psychopharmacology, HYDROXYBUTYRATE 9:211-15 (1994)), and to stimulate growth hormone and prolactin production (U.S. Pat. No. 5,840,331 to Van Cauter, CROSS-REFERENCE TO RELATED et al.). Administration of GHB also is purported to be an APPLICATION effective
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