EP3833370A1 - Compositions for use in the treatment of obesity - Google Patents

Compositions for use in the treatment of obesity

Info

Publication number
EP3833370A1
EP3833370A1 EP19729848.2A EP19729848A EP3833370A1 EP 3833370 A1 EP3833370 A1 EP 3833370A1 EP 19729848 A EP19729848 A EP 19729848A EP 3833370 A1 EP3833370 A1 EP 3833370A1
Authority
EP
European Patent Office
Prior art keywords
extract
withaferin
composition
plant
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19729848.2A
Other languages
German (de)
English (en)
French (fr)
Inventor
Alessandro LAVIANO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nutrintech Ltd
Original Assignee
Nutrintech Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nutrintech Ltd filed Critical Nutrintech Ltd
Publication of EP3833370A1 publication Critical patent/EP3833370A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents

Definitions

  • compositions for use in the treatment of obesity are “Compositions for use in the treatment of obesity”.
  • the present invention relates to compositions comprising Withaferin A and a cinnamon extract and the use thereof for the treatment of obesity, and in general for the reduction of fat mass. Also kits of portions, comprising a first composition including Withaferin A and a second composition including a cinnamon extract, belong to the present invention.
  • Obesity represents a clinical condition characterized by the increase in fat mass and the development of chronic- degenerative pathologies, such as diabetes, arterial hypertension and some forms of tumours ( Pearson-Stuttard J et al, Lancet Endocrinol Diab 2018) .
  • the clinical relevance of obesity is underlined not only by its large prevalence and by its clinical correlations, but even by the lack of an effective medical therapy which could contribute in favouring the change of life styles.
  • a minimum percentage of patients is obese for precise genetic causes. On the contrary, for most part of patients, the obesity causes are to be found in the not healthy life styles, and in particular in the unbalance between energy introduced with diet and energy consumption through physical activity. Under physiological conditions, the excessive consumption of food is prevented by a series of endocrinological mechanisms, thereamong the circulating levels of leptin hormone (Pan WW et al, Nat Rev Neurosci 2018) .
  • Leptin is a polypeptide hormone produced by the adipose tissue proportionally to its sizes. The increase in the circulating levels of leptin triggers the activation of brain areas leading to the decreased appetite and of the caloric intake per os (Pan WW et al, Nat Rev Neurosci 2018) .
  • brown adipose tissue Although the brown adipose tissue is limited in man, the transformation of the white tissue into brown tissue, phenomenon called "browning", was demonstrated after physical stimuli, such as the exposition to cold, or pharmacological stimuli (Thyagarajan B et al, Horm Mol Biol Clin Investig 2017) .
  • Obesity is a clinical and social problem, which does not recognize effective therapies, with the exception of the bariatric and metabolic surgery even if compositions are known which help the weight loss, such as for example the International patent application Nr. W02005/ 107779 which describes a composition for the weight loss based upon Garcinia cambogia extract, Gymnema sylvestre extract and green tea extract.
  • compositions such as for example those described in the patent application US 2011/0052736) are used even for the muscle recovery.
  • the object of the present invention is to provide composition and kit useful for the treatment of obesity and more generally for the reduction of fat mass.
  • the present invention is based upon the search for and identification of a new combination of natural active principles which used in association exert a synergic effect in the reduction of the fat mass as confirmed by experiments on some obese subjects.
  • the present invention relates to compositions comprising Withaferin A and/or an extract of Whitania somnifera including said molecule and a cinnamon extract.
  • the present invention further relates to their use in the prevention and treatment of obesity.
  • the association Withaferin A and/or an extract of Whitania somnifera including said molecule and cinnamon extract provides a natural solution to the clinical problem of obesity through the normalization of brain sensitivity to leptin, with consequent decreased appetite and caloric intake, and increase in energy expenditure through the "browning" of adipose tissue.
  • the present invention describes a composition
  • a composition comprising as main active ingredients the cinnamon extract in association with Withaferin A and/or with an extract of Whitania somnifera including such molecule.
  • Withaferin A is the main component of the extract of Withania somnifera (that is, Ashwaganda in the ayurvedic tradition), in particular of the root and/or leaves which are the portions most commonly used for the preparation of extracts from said plant. Chemically, Withaferin A is a steroid lactone with important biological properties. Withaferin A returns the normal sensitivity to leptin in experimental models of obesity induced by the diet, by reducing the body weight and improving the metabolic profile associated to obesity. Withaferin A has the following structure formula and it could be prepared according to the procedures known to the person skilled in the art .
  • Withaferin A if provided as molecule, as such could be for example administered with a dosing regimen between 50 and 500 mg/die, preferably 300 mg/die (for example lOOmg x 3 times per day, for example one hour before the main meals), alternatively, if provided as extract of Whitania somnifera plant, the dosage of Withaferin A pro die could be administered with a dosing regimen from 2 to 500 mg/die, from 2 to 200 mg/die, from 2 to 100 mg/die, from 2 to 50 mg/die, from 2 to 20 mg/die, from 2 to 10 mg/die, from 2 to 5 mg/die (for example 1-1.5 mg three times per day) .
  • the composition could include Withaferin A as insulated molecule and/or an extract of Withania somnifera including such molecule (for example prepared by means of techniques commonly used in the field such as the aqueous extraction, the hydroalcoholic extraction and the like) , in particular an extract as above defined from root of Whitania somnifera preferably titrated at a certain percentage of Withaferin A.
  • an extract of Withania somnifera including such molecule for example prepared by means of techniques commonly used in the field such as the aqueous extraction, the hydroalcoholic extraction and the like
  • an extract as above defined from root of Whitania somnifera preferably titrated at a certain percentage of Withaferin A.
  • extracts of Whitania somnifera plant can be used, having a content of Withaferin A (and then titrated in Withaferin A) from about 0.2% w/w to 20% w/w.
  • an extract of Whitania somnifera plant suitable to implement the present invention can have a content of Withaferin A from about 0.2% w/w to 15% w/w, from 0.2% w/w to 10% w/w or from 0.2% w/w to 5% w/w.
  • the extract used in the present invention can be an extract or one or more fractions of extract of Whitania somnifera, such as for example an aqueous extract or a hydroalcoholic extract, optionally lyophilised, with a titre in Withaferin A of about 0.2; 0.3, 0.4; 0.5; 0.6; 0.7; 0.8; 0.9; 1 ; 1.5; 2 ; 2.5; 3 ; 3.5; 4 ; 4.5; 5 ; 5.5; 6 ; 6.5; 7; 7.5; 8; 8.5; 9; 9.5; 10; 10.5; 11; 11.5; 12; 12.5; 13; 13.5; 14; 14.5; 15; 15.5; 16; 16.5; 17; 17.5; 18; 18.5; 19; 19.5; 20% w/w of said extract.
  • aqueous extract or a hydroalcoholic extract optionally lyophilised
  • the authors of the present invention have also surprisingly found that by using the extract of Whitania somnifera plant instead of the molecule of Withaferin A it is possible to administer much lower dosages of Withaferin A pro die than those required with Withaferin A as such.
  • the dosage of Withaferin A pro die can be comprised from 2 to 500 mg/die, from 2 to 200 mg/die, from 2 to 100 mg/die, from 2 to 50 mg/die, from 2 to 20 mg/die, from 2 to 10 mg/die, from 2 to 5 mg/die.
  • the person skilled in the art could adapt the amount of extract used in the preparation of the formulations to be administered depending upon the used extract of Whitania somnifera.
  • the used amount of extract can be reduced when the used extract of Whitania somnifera has a high titre in Withaferin A in the shown range, whereas the used amount of extract can be increased when the used extract of Whitania somnifera has a low titre in Withaferin A with respect to the shown range (0.2-20% w/w) .
  • 3 capsules/die can be administered including 150 mg of extract of Whitania somnifera plant titrated at 1% w/w in Withaferin A which correspond to 1.5 mg of Withaferin A per capsule, being equal to a total of 4.5 mg/die.
  • 3 capsules/die can be administered including 10 mg di extract of Whitania somnifera plant titrated at 15% in Withaferin a which correspond to 1.5 mg of Withaferin A equalling to a total of 4.5 mg/die.
  • 8 capsules can be administered including 250 mg of extract of Whitania somnifera plant titrated at 0.2% w/w in Withaferin A which correspond to 0.5 mg of Withaferin A per capsule, equalling to a total of 4 mg/die.
  • the dosage of 4.5 mg/die of Withaferin A if formulated by using an extract of Whitania somnifera as above exemplified can be adapted even during the period of ingestion of the composition of the invention according to the results obtained in time, by decreasing it to 4; 3.5; 3; 2.5; 2 mg/die of Withaferin A if formulated by using an extract of Whitania somnifera, or increased to 5; 5.5; 6 ; 6.5; 7 ; 7.5; 8 ; 8.5; 9 ; 9.5; 10; 15; 20; 25; 30; 50; 100; 200; 300; 400; 500 mg/die of Withaferin A if formulated by using an extract of Whitania somnifera.
  • compositions with different amounts of extract of Whitania somnifera can be implemented so as to allow the administration of more or less high dosages without the treated subject having to ingest an excessive number of unitary doses (for example capsule, opercle, pill, granulate, tablet etc.) per day.
  • unitary doses for example capsule, opercle, pill, granulate, tablet etc.
  • the composition will include even a cinnamon extract, in particular an extract from the cinnamon bark ( Cinnamomum cassia plant or Cinnamomum Verum plant, also called Cinnamomum Zeylanicum) .
  • cinnamon extract induces the "browning" of the subcutaneous adipose tissue of animals with obesity induced by the diet, by producing a significant weight loss.
  • the extract could be prepared according to the procedures known in the state of art, for example it could be a dry or powder extract.
  • an extract of cinnamon bark will be used, prepared with ethanol extraction, in particular having 70% of water, optionally lyophilised.
  • An example of cinnamon extract will include mainly: protocatechuic acid (for example about 17.3 mg/kg), catechin (for example about 302 mg/kg), chlorogenic acid (for example about 25.1 mg/kg), aesculetin (for example about 12.7 mg/kg), quercetin (for example about 180.9 mg/kg) and icarin (for example about 51.1 mg/kg) .
  • the cinnamon extract could be administered for example with a dosing regimen from 50 to 2000 mg/die, in particular 1800 mg/die, preferably in 3-6 separate administrations (for example 600mg x 3 times per day, or 300 mg 6 times per day) .
  • the composition does not comprise at least two, at least three, at least four, at least five or at least six of the following components: Garcinia cambogia extract, Gymnema sylvestre extract, green tea extract, curcumin, resveratrol and aspartic acid, or derivatives thereof.
  • the composition comprises an extract of Withania somnifera plant (preferably from root and leaves) and a cinnamon extract as unique active ingredients for the reduction of the body weight. Therefore, the composition can include other components, such as for example carriers, excipients, stabilizers, preservatives, and the like, but it does not comprise other principles or compounds active in the weight loss or control.
  • the composition of the invention comprises cinnamon extract in any herein defined form, Withaferin A and/or extract of the Whitania somnifera plant comprising Withaferin A (preferably from root) in any herein defined form and at least one or more pharmaceutically acceptable substances selected among excipients, stabilizers, preservatives, glidants, fillers, humectants, disintegrants , binders, retardants, absorption accelerators, adsorbents, lubricants and the like.
  • composition according to the invention can include cinnamon extract in any herein defined form, Withaferin A and/or extract of the Whitania somnifera plant including Withaferin A (preferably from root) in any herein defined form and one or more pharmaceutically acceptable excipients.
  • compositions according to the present invention can be formulated under any form and administration route and associated to any other component, in a variety of ways, preferably they will be formulated for oral use for example as capsules, soft capsules, tablets, pills, gelatines, powders or granules.
  • excipients can be selected for example among those normally used in the state of art and include, but they are not limited thereto: a) carriers, such as for example sodium citrate and calcium phosphate, b) fillers such as for example starch, lactose, microcrystalline cellulose, sucrose, glucose, mannitol, triglycerides and colloidal silica, c) humectants, such as for example glycerol, d) disintegrants , such as alginates, calcium carbonate, starches, derivatives of starch, of cellulose and of polyvinylpyrrolidone, silicates and sodium carbonate e) binders such as carboxymethylcellulose, alginates, gelatine, polyvinylpyrrolidone, sucrose, polymeric derivatives of cellulose, starch derivatives f) retarding agents such as paraffin, cellulose polymers, esters of fatty acids g) absorption accelerators, such as quaternary ammonium compounds, h) wetting
  • solid dosage such as tablets, capsules, soft capsules, gelatines, pills and granules
  • enteric, gastric coatings or coatings of other type known in the state of art can include opacifers and can be of the type to allow the release of the active ingredients only or preferably in a certain tract of the intestine, in case, in a delayed manner.
  • Substances which can allow such delayed use include, but they are not limited thereto, polymers and waxes.
  • the soft capsules could house the antioxidant substances in liquid forms alone or in solutions, suspensions or emulsions of the active substances in a liquid solvent.
  • the soft capsules could be characterized by a casing qualitatively similar to that of the stiff ones but thicker and soft.
  • Liquid forms suitable to an oral administration are for example emulsions, solutions, prepared or extemporaneous suspensions, syrups and elixirs.
  • Excipients suitable to the formulations according to the present invention in liquid forms for oral use include, but they are not limited thereto, diluents such as water or other solvents, solubilizing agents and emulsifying agents selected from ethyl alcohol, polyalcohols, propyl glycol, glycerol, polyethylenglycol and sorbitan esters. These formulations can even include sweeteners and flavours.
  • compositions will be for example a medical device, a food supplement, a nutraceutical , dietetic and nutritional composition, a food product, a beverage, a neutraceutical , a medicament, a medicated food, food for special medical purposes, food, a pharmaceutical composition.
  • the compositions will be mainly intended to be used by the human beings, but they could also be used on animals.
  • the combination of the above-mentioned active ingredients could be used formulated in one single composition according to the various above-described embodiments or in a kit including the different separate ingredients, for example in single compositions such as capsules, pills tablets for sequential or contemporary administration of the different ingredients.
  • compositions could be used/administered/ingested for preventing and/or treating obesity, in particular in female subjects. They could also be used by not obese patients to reduce the fat mass.
  • the combination of active ingredients according to the present invention will be administered with a daily dosing regimen according to the above-mentioned amounts.
  • compositions for oral use will include for example between 10 and 5000 mg of Cinnamon extract per dosage unit and between 10 and 5000 mg of insulated Withaferin A, or 2-500 mg of Withaferin A if formulated by using an extract of Whitania somnifera per dosage unit, preferably between 50 and 500 mg of Cinnamon extract per dosage unit and between 50 and 500 mg of insulated Withaferin A, or 2-100; 2-50; 2-20; 2-10; 2-5 mg of Withaferin A if formulated by using an extract of Whitania somnifera .
  • compositions of the present invention are shown hereinafter.
  • composition for oral use in form of capsule Composition for oral use in form of capsule
  • composition for oral use in form of pill
  • EXAMPLE 3 Composition for oral use in form of pill, capsule, opercle, granulate or tablet
  • the invention relates to, the inventors performed a clinical study by following the protocol described hereinafter. The study was performed with consenting and informed patients and the medical protocol was approved by the ethics committee of the University "SAPIENZA" in Rome.
  • Age comprised between 25 years old and 75 years old
  • the recruitment will exclude the patients having: symptomatic chronic cardiac deficiency (NYHA class III- IV); congenital heart diseases; tacho-brady arrhythmias with poor pharmacological control; neoplasia in progress; acute heart attack or acute coronary syndrome within 3 months preceding the inclusion in the study; acute infections or inflammations in progress; valvulopathy; cognitive deficit or poor compliance to the treatment; concomitant treatment with thyroid hormones or other drugs interfering with metabolism. Pregnant or fertile women, not using adequate contraceptive methods, will be excluded from inclusion.
  • the demographic and clinical features will be synthetized by means of descriptive statistics (average, standard deviation, median, interquartile range) in case of continuous variables and by means of absolute frequencies and percentages in case of categoric variables.
  • the distribution normality of all variables will be tested by using Kolmogorov-Smirnov test.
  • the comparison between percentages will be performed by means of chi-square test or with the exact test of Fisher (if n ⁇ 5) .
  • the correlation coefficients of Pearson or Sperman will be used for analysing the dependence between variables.
  • the intra-subject weight variation will be evaluated by means of a t-test for paired data.
  • the comparison analysis between the two types of intervention will make use of an analysis of the variance for repeated measurements or, if required, not parametric tests.
  • the statistical software R (3.3.2) will be used for the statistical analysis.
  • the study was performed on a sample of 40 subjects.
  • the performed study is a perspective, double-blind study) , cross-over with randomized AB/BA drawing: such mode was selected as at the beginning of a dietary-nutritional programme the adherence is higher and this could constitute a bias.
  • the primary end-point of the study is the variation in the body weight with energy restricted diet and use of the association of extract of Withania somnifera and of extract of cinnamon bark with respect to the body weight with energy restricted diet and placebo.
  • the systemic effects of the association can also be evaluated through markers of inflammation (that is, CRP, ratio neutrophils on lymphocytes) and of sugar metabolism (that is, glycaemia) and lipidic metabolism (that is, total cholesterol and triglycerides) and/or the effects of the association on the abdominal and gluteal circumference.
  • CRP CRP
  • sugar metabolism that is, glycaemia
  • lipidic metabolism that is, total cholesterol and triglycerides
  • the treatment A consists in capsules containing 300 mg of extract of cinnamon bark, 150 mg of extract of the root and the leaves of Withania sominifera plant titrated at about 0.5% in Withaferin A and 10 mg of magnesium stearate, whereas the treatment B in capsules containing an equal dose of starch and cellulose, to be ingested three times per day.
  • a diet is meant determining a loss of 20% of the calories usually introduced by the patient.
  • a diet is processed determining a loss of 20% of the calories usually introduced by the patient.
  • the amount is provided to the patient for 4 weeks of association or placebo (depending upon the results of randomization) .
  • the patient is called again for a medical examination wherein a new clinical and nutritional evaluation is performed.
  • the patient starts the treatment B or A by using the provided material.
  • the patient is examined again and the results are recorded. At this point, the patient exits the study as he/she has completed the protocol, and he/she will continue to be followed by our centre.
  • each patient is subjected to a blood withdrawal apt to evaluate the routine indexes (creatinine, azotemia, uricemia, blood count, triglycerides, total cholesterol, HDL, LDL, glycaemia) .
  • routine indexes creatinine, azotemia, uricemia, blood count, triglycerides, total cholesterol, HDL, LDL, glycaemia.
  • the used cinnamon extract is a dry extract of bark of Cinnamomum Cassia obtained by the extraction ethanol/water such as, for example, the dry extraction of a bark of Cinnamomum Cassia commercialized by FlaNat research.
  • the used extract of Withania somnifera is a dry extract of roots and leaves of Withania somnifera plant obtained by extraction in water and which has the following composition: glycosides Witanolides 3 10% w/w, oligosaccharides 3 32% w/w and aglycone of Witanolide (such as Withaferin A) ⁇ 0.5% w/w such as, for example, the dry extract of roots and leaves of Withania somnifera plant commercialized by Natreon (Sensoril®) .

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Hematology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Child & Adolescent Psychology (AREA)
  • Obesity (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP19729848.2A 2018-05-14 2019-05-14 Compositions for use in the treatment of obesity Withdrawn EP3833370A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT102018000005336A IT201800005336A1 (it) 2018-05-14 2018-05-14 Composizioni per uso nel trattamento dell’obesità
PCT/IB2019/053980 WO2019220335A1 (en) 2018-05-14 2019-05-14 Compositions for use in the treatment of obesity

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EP3833370A1 true EP3833370A1 (en) 2021-06-16

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CN112022842A (zh) * 2020-09-23 2020-12-04 中国农业大学 原儿茶酸用于制备增加能量代谢和帮助寒冷环境中维持体温的药物中的应用
KR20230129831A (ko) * 2022-03-02 2023-09-11 주식회사 에이치엘사이언스 아쉬아간다 추출물 및 구절초 추출물의 복합물(asc복합물)을 유효성분으로 포함하는 비만의 예방, 개선 또는 치료용 조성물
KR102614233B1 (ko) * 2022-11-25 2023-12-19 (주)엔에스티바이오 12-디옥시위타스트라모놀라이드와 그 유도체를 포함하는 체지방 감소용 조성물

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US9700590B2 (en) * 2004-03-01 2017-07-11 In Ingredients, Inc. Methods and materials for reducing or eliminating risk factors associated with syndrome X
WO2005107779A2 (en) * 2004-04-30 2005-11-17 New Hc Formulations Ltd. Weight loss composition and method of inducing weight loss
US20110064720A1 (en) * 2009-09-16 2011-03-17 Daniel Moses Amato Dietary Supplement Compositions and Methods of Making and Using the Same
CA2931826C (en) * 2013-11-26 2021-11-16 The Children's Medical Center Corporation Compounds for the treatment of obesity and methods of use thereof
US10159653B2 (en) * 2013-12-12 2018-12-25 Nestec S.A. Methods and compositions for increasing energy expenditure using cinnamaldehyde

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