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(12) Patent Application Publication (10) Pub. No.: US 2008/0033011 A1 Tung (43) Pub

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(12) Patent Application Publication (10) Pub. No.: US 2008/0033011 A1 Tung (43) Pub US 2008003301 1A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0033011 A1 Tung (43) Pub. Date: Feb. 7, 2008 (54) NOVEL BENZODI1,3-DIOXOL (60) Provisional application No. 60/704,073, filed on Jul. DERVATIVES 29, 2005. Publication Classification (75) Inventor: Roger Tung, Lexington, MA (US) (51) Int. Cl. A6II 3L/435 (2006.01) Correspondence Address: A6IP 5/30 (2006.01) EDWARDS ANGELL PALMER & DODGE (52) U.S. Cl. .............................................................. S14/321 LLP P.O. BOX SS874 (57) ABSTRACT BOSTON, MA 02205 (US) The present invention relates to an isotopologue of paroX etine substituted with deuterium at the methylene carbon of (73) Assignee: cost Flymaceuticals Inc., Lexing- the benzodioxol ring. The isotopologues of this invention s selective serotonin reuptake inhibitors (SSRIs) and possess (21) Appl. No.: 11/775,857 unique biopharmaceutical and metabolic properties com y x- - - 9 pared to paroxetine. They may also be used to accurately (22) Filed: Jul. 10, 2007 determine the concentration of paroxetine in biological fluids and to determine metabolic patterns of paroxetine and Related U.S. Application Data its isotopologues. The invention further provides composi tions comprising these deuterated isotopologues and meth (63) Continuation-in-part of application No. 1 1/704,554, ods of treating diseases and conditions that are responsive to filed on Feb. 8, 2007, which is a continuation-in-part increased neuronal serotonin transmission, alone and in of application No. 11/498.334, filed on Jul. 31, 2006. combination with additional agents. A. 60 A. 7W -8- Control 50-r-8 r Cmpd 1 - 0.5uM rer Cmpd 1 - 2puM VA r&r Cmpd 1 - 5uM O O rŠr Cmpd 1 - 1 OuM 40-"*" Cmpd 1 - 25uM -O-Paroxetine - 0.5uM -- Paroxetine - 2puM V V - A - Paroxetine - 5uM -o- Paroxetine - 1 OuM 30 V- ParOxetine - 25LM O 2 4 6 8 10 12 14 16 18 20 22 Pre-Incubation Time (min) Patent Application Publication Feb. 7, 2008 Sheet 1 of 2 US 2008/0033011 A1 FIG. I. A 60 VA O AV -8- Control C 50 rer"Cmpd Cmpd 1 - 2M0.5M N. rsr Cmpd 1 - 5uM O O rŠr Cmpd 1 - 1 OuM VA 40-"*- Cmpd 1 - 25uM -O-Paroxetine - 0.5uM Paroxetine - 2puM V V - A - Paroxetine - 5uM -o- Paroxetine - 1 OuM 30 V - ParOxetine - 25UM O 2 4 6 8 1 O 12 14 16 18 20 22 Pre-Incubation Time (min) Patent Application Publication Feb. 7, 2008 Sheet 2 of 2 US 2008/0033011 A1 FIG. I (Cont'd) O 5 1 O 15 2O Pre-Incubation Time (min) US 2008/0033011 A1 Feb. 7, 2008 NOVEL BENZODI1,3-DIOXOL DERIVATIVES (hot flashes) (Stearns, V et al., J. Clin Oncol, 2005, 23(28):6919; Stearns.V et al., JAMA, 2003, 289(21):2827). CROSS REFERENCE TO RELATED 0004 Definitions and descriptions of these conditions are APPLICATIONS known to the skilled practitioner and are further delineated, 0001. This application is a continuation-in-part of for instance, in the above patents and patent applications and copending U.S. patent application Ser. No. 1 1/704,554, filed references contained therein. See also: Harrison's Principles Feb. 8, 2007, which is a continuation-in-part of copending of Internal Medicine 16th Edition, Kasper D L et al. Eds. U.S. patent application Ser. No. 1 1/498.334, filed Jul. 31, 2004, McGraw-Hill Professional; and Robbins & Cotran 2006, which claims benefit of U.S. provisional application Pathologic Basis of Disease, Kumar V et al. Eds., 2004, W. 60/704,073, filed Jul. 29, 2005. The contents of each of these B. Saunders. applications are incorporated by reference herein. 0005 The combination of paroxetine with additional agents extends or enhances its utility in the treatment or BACKGROUND OF THE INVENTION prevention of depression, hypertension, generalized anxiety disorder, phobias, posttraumatic stress syndrome, avoidant 0002 Paroxetine has the structure: personality disorder, sexual dysfunction, eating disorders (including bulimia, anorexia nervosa, and binge eating), obesity, chemical dependencies, cluster headache, migraine, pain (including neuropathic pain, diabetic nephropathy, post-operative pain, psychogenic pain disorders, and chronic pain syndrome), Alzheimer's disease, obsessive-compulsive disorder, panic disorder with or without agoraphobia, memory disorders, Parkinson's diseases, endocrine disor ders, vasospasm, cerebellar ataxia, gastrointestinal tract dis orders, negative symptoms of schizophrenia, premenstrual syndrome, Fibromyalgia Syndrome, urinary incontinence (including stress incontinence), Tourette’s syndrome, tricho tillomania, kleptomania, male impotence, cancer, chronic N paroxysmal hemicrania and headache in a mammal, sleep related breathing disorders, cognitive deficits due to aging, and is chemically described variously as (-)-trans-4R-(4'- stroke, head trauma, neurodegenerative diseases, Schizo fluorophenyl)-3S-(3',4'-methylenedioxyphenoxy)methyl phrenia, anxiety, aggression, stress, disorders of ther piperidine; (3S,4R)-3-((benzod1.3dioxol-5-yloxy)im moregulation, respiratory disease, bipolar disorder, psycho ethyl)-4-(4-fluorophenyl)piperidine: trans-(-)-3-(1,3- sis, sleep disorders, mania (including acute mania), bladder benzodioxol-5-yloxy)methyl-4-(4-fluorophenyl)piperidine. disorder, genitourinary disorder, cough, emesis, nausea, psy Paroxetine and its pharmaceutically acceptable addition chotic disorders such as paranoia and manic-depressive salts, hydrates, and polymorphs thereof, are known as useful illness, tic disorder, diabetic cardiomyopathy, diabetic ret selective serotonin reuptake inhibitors (SSRI). This com inopathy, cataracts, myocardial infarction, prolonged pound and pharmaceutical compositions comprising it have fatigue, chronic fatigue, chronic fatigue syndrome, prema utility in the treatment of depression, obsessive-compulsive ture ejaculation, dysphoria, post partum depression, Social disorder, generalized anxiety, post-traumatic stress, major phobia, disruptive behavior disorders, impulse control dis orders, borderline personality disorder, attention deficit dis depression, panic disorder, Social phobia, premenstrual Syn orders without hyperactivity, Shy-Drager Syndrome, cere drome, cardiac disorders, non-cardiac chest pain, Smoking bral ischemia, spinal cord trauma, Huntington's Chorea, (both to cause cessation and prevent relapses), reducing amyotrophic lateral Sclerosis, AIDS-induced dementia, mus platelet activation states, alcoholism and alcohol depen cular spasms, convulsions, perinatal hypoxia, hypoxia, car dence, psychiatric syndromes (including anger, rejection diac arrest, hypoglycemic neuronal damage, ocular damage sensitivity, and lack of mental or physical energy), late luteal and retinopathy, brain edema, tardive dyskinesia, cerebral phase dysphoric disorder, premature ejaculation, senile deficits Subsequent to cardiac bypass Surgery and grafting, dementia, obesity, Parkinson's Disease, and canine affective affective disorders, mood disorders, agoraphobia without aggression. See US Food and Drug Administration product history of panic disorder, and acute stress disorders. These label for New Drug Application (NDA) Nos. 020031, additional agents are also useful for reducing the side effects 020710, and 020936; and U.S. Pat. Nos. 4,007, 196; 4,745, of paroxetine, enhancing or potentiating its activity, or 122; 5,371,092: 5,276,042; 5,788,986; 5,554,383; 5,789, increasing its duration of pharmacological action. U.S. Pat. 449; 6,121,291; 6,071,918; 6.245,782; 6,300,343; 6,316, Nos. 5,776,969; 5,877,171; 5,977,099; 5,962,514; 6,169, 469; and 6,372,763. O98; 5,958,429; 5,945,416; 6,066,643; 5,817,665; 6,034,09: 0003) Additionally disclosed uses for paroxetine include 5,990,159; 6,001,848; 6,011,054; 6,080,736: 6,162,805; methods of inhibiting cancer cell growth, stimulating bone 6,136,861; 6,147,072: 6,218,395; 6,169,105; 6,191,133; formation by osteoblast stimulation, treatment of dermato 6,239,126; 6.242,44; 6,372,919; 6,369,051; 6,358,944; logical diseases or disorders such as hyperproliferative or 6,121,259; 6,174,882; 6,348,455; 6,352,984; 6,468,997: inflammatory skin diseases, and treatment of premature 6,403,597; 6,395,788; 6.541,523: 6,127,385; 6,395,752: female orgasm: see United States Patent Publications 6,380,200; 6,387,956; 6,444,665; 6,541478; 6,541,043; 20040127573; 20040127573; 200500 13853; 20040029860; 6,562,813; 6,579,899; 6,627,653; 6,649,614; 6,667,329; and 2005.0054688. Paroxetine has also been disclosed as 6,727,242; 6,656,951: 6,780,860; 6,815,448; 6,821,981; useful in the treatment of menopausal vasomotor symptoms 6,861,427; 6,878,732; and 6,894,053. US 2008/0033011 A1 Feb. 7, 2008 0006 Further disclosed are additional combinations of tion (NDA) Nos. 020031, 020710, and 020936: Wag paroxetine with other agents extending or enhancing its staff A J et al., Drugs, 2002, 62:655; Katona C and utility in the treatment or prevention of autism, dyski Livingston G, J Affect Disord, 2002, 69:47. nesia, dysthymic disorder, obesity due to genetic or environmental causes, polycystic ovary disease, cran 0010. Following oral administration to humans, paroxet iopharyngioma, Prader-Willi Syndrome, Froehlich's ine is well absorbed, after which it undergoes extensive Syndrome, Type II diabetes, growth hormone defi oxidative and phase II metabolism. Its major metabolic ciency, Turner's Syndrome; pro-inflammatory cytokine pathway proceeds by oxidative cleavage of the benzodioxol Secretion or production, jet lag, insomnia, hyperSom ring to forming a catechol metabolite. Subsequent phase II nia, nocturnal enuresis, restless-legs syndrome, vaso metabolism involves mainly methylation, glucuronidation
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