106650-56-0

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• A study and identification of potential by-products of sibutramine
• In the synthesis and process development of sibutramine (9), the isolation and characterization of two potential by-products namely heptane dinitriles (4a-b) and bis-cyclobutyl alkylamine (10) have been studied. The key steps in the synthesis of sibutramine which have contributed to the formation of above by-products are cycloalkylation of 4-chlorophenyl acetonitrile (1) and tandem Grignard reduction on 1-(4-chlorophenyl)cyclobutyl carbonitrile (3).
• Reddy, G. Om,Sarma,Chandrasekhar,Babu, J. Moses,Prasad,Raju, C.M. Haricharan

• p. 488 - 492

  (1999)
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• Novel diacid accelerated borane reducing agent for imines
• A remarkable effect of diacids in modulating the reactivity of borane has been discovered. This novel process provides a rapid and excellent access for reduction of a variety of imines with different functionalities.
• Lu, Zhi-Hui,Bhongle, Nandkumar,Su, Xiping,Ribe, Seth,Senanayake, Chris H

• p. 8617 - 8620

  (2002)
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• Resolutions of sibutramine with enantiopure tartaric acid derivatives: chiral discrimination mechanism
• Abstract The resolution of sibutramine 1 was investigated with enantiopure tartaric acid derivatives. Based on the resolving efficiency assay using a 'Dutch resolution', O,O′-di-p-anisoyl-(R,R)-tartaric acid (R,R)-DMTA was identified as an effective resol
• Hu, Yu,Yuan, Jia-Jie,Sun, Xiao-Xia,Liu, Xi-Mei,Wei, Zhen-Hong,Tuo, Xun,Guo, Hui

• p. 791 - 796

  (2015)
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• COMPOSITIONS, SYNTHESIS, AND METHODS OF USING PHENYLCYCLOALKYLMETHYLAMINE DERIVATIVES
• The present invention provides novel phenylcycloalkylmethylamme derivatives, and methods of preparing phenylcycloalkylmethylamme derivatives. The present invention also provides methods of using phenylcycloalkylmethylamme derivatives and compositions of phenylcycloalkylmethylamme derivatives. The pharmaceutical compositions of the compounds of the present invention can be used for treating and/or preventing obesity and obesity related co- morbid indications and depression and depression related co-morbid indications.
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• Page/Page column 32-33

  (2013/07/19)
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• Compositions, Synthesis, and Methods of Using Cycloalkylmethylamine Derivatives
• The present invention provides novel cycloalkylmethylamine derivatives, and methods of preparing cycloalkylmethylamine derivatives. The present invention also provides methods of using cycloalkylmethylamine derivatives and compositions of cycloalkylmethylamine derivatives. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications and depression and depression related co-morbid indications.
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• Page/Page column 24

  (2012/07/14)
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• SYNTHESIS, METHODS OF USING, AND COMPOSITIONS OF CYCLOALKYLMETHYLAMINES
• The present invention provides novel cycloalkylmethylamine analogs, and methods of preparing cycloalkylmethylamine analogs. The present invention also provides methods of using cycloalkylmethylamine analogs and compositions of cycloalkylmethylamine analogs. The pharmaceutical compositions of the compounds of the present invention can be advantageously used for treating and/or preventing obesity and obesity related co-morbid indications.
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• Page/Page column 44-45

  (2008/06/13)
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• A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1,2,3-oxathiazolidme-2-oxide: Practical asymmetric synthesis of (R)-sibutramine
• A novel and direct approach for the asymmetric synthesis of (R)-sibutramine via chiral amine 5 using N-tosyl-1,2,3-oxathiazolidine-2-oxide (13) as a recyclable chiral auxiliary is described. Chiral sulfinate imine 16e was obtained by treatment of 13e with
• Han, Zhengxu,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.

• p. 327 - 333

  (2012/12/22)
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• USE OF (S)-DIDESMETHYLSIBUTRAMINEFOR TREATING, PREVENTING AND MANAGING A SLEEP DISORDER
• This invention relates, in part, to methods of treating, preventing and/or managing a sleep disorder using enantiomerically pure (S)-didesmethylsibutramine, or a pharmaceutically acceptable salt, hydrate, solvate, clathrate or prodrug thereof. Specific me
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• Page/Page column 29

  (2008/06/13)
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• DOPAMINE-AGONIST COMBINATION THERAPY FOR IMPROVING SLEEP QUALITY
• The present invention generally to pharmaceutical compositions comprising a dopamine agonist and sedative agent. In a preferred embodiment, the dopamine agonist is optically pure (S)-didesmethylsibutramine. In a preferred embodiment, the sedative agent is
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• Page/Page column 89

  (2008/06/13)
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• Treatment of neuropathic pain or fibromyalgia
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1 and R2 are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating fibromyalgia or neuropathic pain, such as pain associated with diabetes mellitus, shingles, nerve injury and varied peripheral neuropathies.
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• (2008/06/13)
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• SIBUTRAMINE FREE BASE IN CRYSTALLINE FORM AND ITS PHARMACEUTICAL USE
• Sibutramine, N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethyl-amine, free base in crystalline form, compositions containing the same and uses thereof.
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• Page 8

  (2008/06/13)
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• Therapeutic agents
• The present invention provides a method of treating and preventing obesity and related co-morbid conditions comprising the administration of a therapeutically effective amount of one or more monoamine reuptake inhibitors which are serotonin reuptake inhibitors and/or noradrenaline reuptake inhibitors and a 5-HT1A agonist to a patient in need thereof.
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• (2008/06/13)
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• Method of controlling weight gain associated with therapeutic drugs
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1 and R2 are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating weight gain associated with treatment with certain drug therapy, including the use of tricyclic antidepressants, lithium, sulphonylureas, beta-adrenergic blockers, certain steroid contraceptives, corticosteroids, insulin, cyproheptadine, sodium valproate, neuroleptics, phenothiazine or piztifen.
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• (2008/06/13)
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• Weight loss after pregnancy
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1 and R2 are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for aiding weight loss after pregnancy.
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• (2008/06/13)
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• Method of using and compositions comprising (-) sibutramine optionally in combination with other pharmacologically active compounds
• This invention encompasses methods for the treatment and prevention of disorders that include, but are not limited to, eating disorders; weight gain; obesity; irritable bowel syndrome; obsessive-compulsive disorders; platelet adhesion; apnea; affective di
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• (2008/06/13)
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• Methods of using and compositions comprising (+) sibutramine optionally in combination with other pharmacologically active compounds
• This invention encompasses methods for the treatment and prevention of disorders that include, but are not limited to, eating disorders; weight gain; obesity; irritable bowel syndrome; obsessive-compulsive disorders; platelet adhesion; apnea; affective disorders such as attention deficit disorders, depression, and anxiety; male and female sexual function disorders; restless leg syndrome; osteoarthritis; substance abuse including nicotine and cocaine addiction; narcolepsy; pain such as neuropathic pain, diabetic neuropathy, and chronic pain; migraines; cerebral function disorders; chronic disorders such as premenstrual syndrome; and incontinence. The invention further encompasses pharmaceutical compositions and dosage forms which comprise optically pure (+) sibutramine, optionally in combination with a phosphodiesterase inhibitor or a lipase inhibitor.
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• (2008/06/13)
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• Methods and compositions for the treatment and prevention of sexual dysfunction
• Methods are disclosed for the treatment and prevention of sexual. The methods comprise the administration of a dopamine reuptake inhibitor and optionally an additional pharmacologically active compound. Pharmaceutical compositions and dosage forms are also disclosed that comprise a dopamine reuptake inhibitor and optionally an additional pharmacologically active compound. Preferred dopamine reuptake inhibitors are racemic or optically pure sibutramine metabolites and pharmaceutically acceptable salts, solvates, and clathrates thereof. Preferred additional pharmacologically active compounds include drugs that affect the central nervous system, such as 5-HT3antagonists.
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• (2008/06/13)
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• METHODS OF USING AND COMPOSITIONS COMPRISING SIBUTRAMINE METABOLITES OPTIONALLY IN COMBINATION WITH OTHER PHARMACOLOGICALLY ACTIVE COMPOUNDS
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• (2008/06/13)
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• Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction
• Methods are disclosed for the treatment and prevention of male and female sexual function disorders which comprise a racemic or optically pure sibutramine metabolite and a phosphodiesterase inhibitor.
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• (2008/06/13)
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• Salts of sibutramine metabolites, methods of making sibutramine metabolites and intermediates useful in the same, and methods of treating pain
• Methods of making and using racemic and optically pure metabolites of sibutramine, and pharmaceutically acceptable salts, solvates, and clathrates thereof, are disclosed. Pharmaceutical compositions and dosage forms are also disclosed which comprise a dopamine reuptake inhibitor, such as a racemic or optically pure sibutramine metabolite, and optionally an additional pharmacologically active compound.
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• (2008/06/13)
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• TREATMENT OF PULMONARY HYPERTENSION
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• (2008/06/13)
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• Method of treating eating disorders
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating eating disorders, such as anorexia nervosa, bulimia nervosa, weight-gain after smoking cessation, snacking or binge eating.
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• (2008/06/13)
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• Treatment of chronic fatigue syndrome
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating chronic fatigue syndrome.
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• (2008/06/13)
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• Method of treating anxiety disorders
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate), including individual enantiomers and racemates thereof, is used for treating anxiety disorders.
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• (2008/06/13)
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• Method of treating sleep apnoea
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl, including individual enantiomers or racemates thereof, (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride optionally in the form of its monohydrate) is used for treating sleeping disorders including sleep apnoea and snoring.
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• (2008/06/13)
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• Treatment to lower platelet adhesiveness
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl) cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for decreasing platelet adhesiveness.
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• (2008/06/13)
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• Method of treating sexual dysfunction
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate), including individual enantiomers and racemates thereof, is used for treating sexual dysfunction.
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• (2008/06/13)
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• Treatment of orthostatic hypotension
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating orthostatic hypotension.
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• (2008/06/13)
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• Control of metabolism
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl ]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating metabolic disorders, such as increased non-exercise activity thermogenesis or increased metabolic rate.
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• (2008/06/13)
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• Treatment of premenstrual syndrome
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1 and R2 are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating premenstrual syndrome.
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• (2008/06/13)
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• Treatment of pharmacology of drug misuse and other addictive disorders
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for exampleN,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating disorders arising from drug misuse or other addictive disorders.
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• (2008/06/13)
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• Treatment of menstrual function
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating menstrual function and infertility.
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• (2008/06/13)
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• Treatment of gallstones
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating gallstones, particularly gallstones associated with weight loss or associated with gall bladder disease related to obesity.
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• (2008/06/13)
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• Treatment of pain
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating pain such as low back pain.
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• (2008/06/13)
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• Treatment of cardiovascular disease
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating cardiovascular disease, such as dyslipidaemia or carotid intimal medial thickening.
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• (2008/06/13)
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• Treatment of hyperactivity disorders
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating hyperactivity disorders, such as attention deficit hyperactivity disorder and hyperkinetic disorder.
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• (2008/06/13)
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• First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis
• A practical synthesis of enantiomerically pure (R)-desmethylsibutramine [(R)-DMS] and (S)-desmethylsibutramine [(S)-DMS] is outlined along with an improved synthesis of racemic desmethylsibutramine. This route was used for kilo-scale production of enantio
• Han, Zhengxu,Krishnamurthy, Dhileepkumar,Pflum, Derek,Fang, Qun K.,Butler, Hal,Cameron,Wald, Stephen A.,Senanayake, Chris H.

• p. 107 - 109

  (2007/10/03)
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• Methods of treating and preventing attention deficit disorders
• Methods are disclosed for the treatment and prevention of affective disorders with racemic or optically pure sibutramine metabolites and pharmaceutically acceptable salts, solvates, and clathrates thereof.
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• (2008/06/13)
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• Treatment of osteoarthritis
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating osteoarthritis or gout.
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• (2008/06/13)
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• Treatment of hiatial hernia
• A compound of formula I or a pharmaceutically acceptable salt thereof in which R1and R2are independently H or methyl (for example N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl amine hydrochloride optionally in the form of its monohydrate) is used for treating hiatial hernias and reflux esophagitis.
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• (2008/06/13)
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• Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites
• Synthetic routes to N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methyibutyl}-N-methylamine2, 1-[1-(4-chiorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard-reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.
• Jeffery, James E.,Kerrigan, Frank,Miller, Thomas K.,Smith, Graham J.,Tometzki, Gerald B.

• p. 2583 - 2589

  (2007/10/03)
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