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FR2882261A1 - Use of cannabinoid receptor antagonists, preferably rimonabant or N-piperidino-5-(4-bromophenyl)-1- (2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide, for the preparation of drugs in the treatment and prevention of type-2 diabetes - Google Patents

Use of cannabinoid receptor antagonists, preferably rimonabant or N-piperidino-5-(4-bromophenyl)-1- (2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide, for the preparation of drugs in the treatment and prevention of type-2 diabetes Download PDF

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Publication number
FR2882261A1
FR2882261A1 FR0501861A FR0501861A FR2882261A1 FR 2882261 A1 FR2882261 A1 FR 2882261A1 FR 0501861 A FR0501861 A FR 0501861A FR 0501861 A FR0501861 A FR 0501861A FR 2882261 A1 FR2882261 A1 FR 2882261A1
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Prior art keywords
rimonabant
cannabinoid
administration
receptor antagonist
dichlorophenyl
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Granted
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FR0501861A
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French (fr)
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FR2882261B1 (en
Inventor
Corinne Hanotin
Pierre Rosenzweig
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Sanofi Aventis France
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Sanofi Aventis France
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Priority to FR0501861A priority Critical patent/FR2882261B1/en
Priority to FR0504942A priority patent/FR2882264A1/en
Priority to FR0505228A priority patent/FR2882265B1/en
Priority to AU2006215444A priority patent/AU2006215444A1/en
Priority to EP06709344A priority patent/EP1853264A1/en
Priority to PCT/FR2006/000376 priority patent/WO2006087481A1/en
Priority to JP2007555669A priority patent/JP2008530189A/en
Priority to MX2007009996A priority patent/MX2007009996A/en
Priority to UY29386A priority patent/UY29386A1/en
Priority to CA002597245A priority patent/CA2597245A1/en
Priority to CNA2006800052531A priority patent/CN101119727A/en
Priority to TW095105631A priority patent/TW200640457A/en
Priority to ZA200707012A priority patent/ZA200707012B/en
Priority to BRPI0608183-5A priority patent/BRPI0608183A2/en
Priority to EA200701781A priority patent/EA011618B1/en
Priority to KR1020077018993A priority patent/KR20070104913A/en
Priority to ARP060100611A priority patent/AR053812A1/en
Publication of FR2882261A1 publication Critical patent/FR2882261A1/en
Priority to TNP2007000297A priority patent/TNSN07297A1/en
Priority to US11/832,865 priority patent/US20080015229A1/en
Priority to CR9293A priority patent/CR9293A/en
Priority to IL185401A priority patent/IL185401A0/en
Priority to MA30158A priority patent/MA29262B1/en
Priority to NO20074767A priority patent/NO20074767L/en
Application granted granted Critical
Publication of FR2882261B1 publication Critical patent/FR2882261B1/en
Priority to US12/402,988 priority patent/US20090197917A1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/155Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/64Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Use of cannabinoid receptor antagonists (I), preferably rimonabant or N-piperidino-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide, for the preparation of drugs in the treatment and prevention of type-2 diabetes. An independent claim is included for a pharmaceutical composition comprising cannabinoid receptor antagonists and active ingredients. ACTIVITY : Antidiabetic. MECHANISM OF ACTION : Cannabinoid receptor antagonists.

Description

2882261 12882261 1

Claims (3)

UTILISATION D'UN DERIVE DU PYRAZOLE POUR LA PREPARATION DE MEDICAMENTS UTILES DANS LA PREVENTION ET LE TRAITEMENT DU DIABETE DU TYPE 2. La présente invention a pour objet l'utilisation d'un composé antagoniste des récepteurs CB 1 aux cannabinoïdes, dérivé du pyrazole, pour la préparation de médicaments utiles dans la prévention et le traitement du diabète de type 2 ou diabète non insulino-dépendant. Le diabète de type 2 se caractérise par des troubles de l'insulinosécrétion associés à des troubles de la sensibilité à l'insuline ou insulino-résistance. L'insulino-résistance est aggravée par une hyperglycémie et par des taux élevés d'acides gras libres circulants et de triglycérides stockés. Selon la présente invention, par antagoniste des récepteurs aux cannabinoïdes dérivés du pyrazole, on entend un composé choisi parmi le Npipéridino-5-(4- chlorophényl)-I-(2,4-dichlorophényl)-4-methylpyrazole-3carboxamide dont la dénomination commune internationale est rimonabant, décrit dans le brevet européen 656354 et le N-pipéridino-5-(4-bromophényl) -1-(2,4-dichlorophényl)-4- ethylpyrazole-3-carboxamide, décrit dans le brevet européen 1150961. Des études cliniques réalisées avec le rimonabant ont montré qu'il agit sur la prise alimentaire sur le plan quantitatif et qualitatif et réduit le poids corporel de patients obèses (G. Le Fur, 2003, 35, First European Workshop on Cannabinoid Research, Madrid, Spain, 4-5 avril 2003 et Heshmati H.M. et al., Obesity Research, 2001, 9 (suppl. 3), 70. Il a maintenant été trouvé qu'un antagoniste des récepteurs CB1 aux cannabinoïdes, dérivés du pyrazole, choisi parmi le rimonabant et le Npipéridino-5-(4-bromophényl)-1-(2,4-dichlorophényl)-4-éthylpyrazole-3carboxamide, présente des propriétés antidiabétiques. Ainsi, selon la présente invention, un composé antagoniste des récepteurs CB1 aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le N-pipéridino- 5-(4-bromophényl)-1-(2,4-dichlorophényl)-4-éthylpyrazole3-carboxamide, peut être utilisé pour la préparation de médicaments utiles pour prévenir et traiter le diabète de type 2. Les compositions pharmaceutiques selon la présente invention contiennent une dose efficace d'un composé antagoniste des récepteurs CB1 aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le Npipéridino-5-(4-bromophényl)-1-(2,4- 2882261 2 dichlorophényl)-4éthylpyrazole-3-carboxamide, ainsi qu'au moins un excipient pharmaceutiquement acceptable. Lesdits excipients sont choisis selon la forme pharmaceutique et le mode d'administration souhaité, parmi les excipients habituels qui sont connus de l'Homme du métier. Dans les compositions pharmaceutiques de la présente invention pour l'administration orale, sublinguale, sous-cutanée, intramusculaire, intraveineuse, topique, locale., intratrachéale, intranasale, transdermique ou rectale, le principe actif peut être administré sous forme unitaire d'administration, en mélange avec des excipients pharmaceutiques classiques, aux animaux et aux êtres humains pour la prévention ou le traitement du diabète de type 2. Les formes unitaires d'administration appropriées comprennent les formes par voie orale telles que les comprimés, les gélules molles ou dures, les poudres, les granules et les solutions ou suspensions orales, les formes d'administration sublinguale, buccale, intratrachéale, intraoculaire, intranasale, par inhalation, les formes d'administration topique, transdermique, sous-cutanée, intramusculaire ou intraveineuse, les formes d'administration rectale et les implants. Pour l'application topique, on peut utiliser les composés selon l'invention dans des crèmes, gels, pommades ou lotions. Les formes pour l'administration orale telles que les gélules ou comprimés sont préférées. Plus particulièrement, on préfère des gélules ou des comprimés contenant le rimonabant à une dose comprise entre 5 et 50 mg, plus particulièrement les doses de 10 à 30 mg, notamment la dose de 20 mg. Pour l'utilisation selon la présente invention, un antagoniste des récepteurs aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le N-pipéridino-5-(4- bromophényl)-1-(2,4-dichlorophényl)-4éthylpyrazole-3-carboxamide, peut être associé à un autre principe actif choisi parmi l'une des classes thérapeutiques suivantes: - un hypolipémiant ou un hypocholestérolémiant; - un autre antidiabétique; -un autre agent anti-obésité. Ainsi, la présente invention a également pour objet des compositions pharmaceutiques contenant en association un antagoniste des récepteurs CB1 aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le N-pipéridino-5-(4- 2882261 3 bromophényl)-1-(2,4-dichlorophényl)-4éthylpyrazole-3-carboxamide, et un autre principe actif choisi parmi l'une des classes thérapeutiques suivantes: - un hypolipémiant ou un hypocholestérolémiant; - un autre antidiabétique; -un autre agent antiobésité. Par hypolipémiant ou hypocholestérolémiant, on entend un composé choisi parmi les fibrates tels que alufibrate, béclobrate, bézafibrate, ciprofibrate, clinofibrate, clofibrate, étofibrate, fénofibrate; les statines (inhibiteurs de HMG-CoA reductase), telles que atorvastatine, fluvastatine sodium, lovastatine, pravastatine, rosuvastatine, simvastatine, ou un composé tel que acipimox, aluminum nicotinate, azacostérol, cholestyramine, dextrothyroxine, méglutol, nicéritrol, nicoclonate, acide nicotinique, béta-sitosterin, tiadénol. Par autre antidiabétique, on entend un composé appartenant à l'une des classes suivantes: les sulfonylurées, les biguanidines, les inhibiteurs d'alpha glucosidase, les thiazolidinedione, les métiglinides, tel que acarbose, acétohexamide, carbutamide, chlorpropamide, glibenclamide, glibornuride, gliclazide, glimépiride, glipizide, gliquidone, glisoxepide, glybuzole, glymidine, métahexamide, metformine, miglitol, natéglinide, pioglitazone, répaglinide, rosiglitazone, tolazamide, tolbutamide, voglibose. Par autre agent anti-obésité, on entend un composé tel que amfépramone, benfluorex, benzphétamine, indanorex, mazindole, méfénorex, méthamphétamine, D-norpseudoéphédrine, orlistat, sibutramine ou un autre antagoniste des récepteurs CB1 aux cannabinoïdes. Selon un autre mode de réalisation particulier, la présente invention a pour objet une composition pharmaceutique contenant en association le rimonabant et la metformine, ou le rimonabant et une sulfonylurée telle que acétohexamide, carbutamide, c:hlorpropamide, glibenclamide, glibornuride, gliclazide, glimépiride, glipizide, tolazamide, tolbutamide, pour le traitement du diabète de type 2. Selon un autre aspect de l'invention, l'antagoniste des récepteurs aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le Npipéridino-5-(4- bromophényl)-1-(2,4-dichlorophényl)-4-éthylpyrazole-3carboxamide, et l'autre principe actif associé peuvent être administrés de manière simultanée, séparée ou étalée dans le temps. On entend par "utilisation séparée" l'administration, en même temps, des deux composés de la composition selon l'invention, chacun compris dans une forme pharmaceutique distincte.USE OF A PYRAZOLE DERIVATIVE FOR THE PREPARATION OF MEDICAMENTS USEFUL IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES The subject of the present invention is the use of a pyrazole-derived cannabinoid CB 1 receptor antagonist compound, for the preparation of drugs useful in the prevention and treatment of type 2 diabetes or non-insulin-dependent diabetes. Type 2 diabetes is characterized by insulin secretion disorders associated with insulin sensitivity disorders or insulin resistance. Insulin resistance is aggravated by hyperglycemia and high levels of circulating free fatty acids and stored triglycerides. According to the present invention, a cannabinoid receptor antagonist derived from pyrazole means a compound chosen from Npiperidino-5- (4-chlorophenyl) -I- (2,4-dichlorophenyl) -4-methylpyrazole-3-carboxamide whose denomination International common is rimonabant, described in European Patent 656354 and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide, described in European Patent 1150961. Clinical studies with rimonabant have shown that it acts on quantitative and qualitative food intake and reduces the body weight of obese patients (Le Fur, 2003, 35, First European Workshop on Cannabinoid Research, Madrid, Spain, April 4-5, 2003 and Heshmati HM et al., Obesity Research, 2001, 9 (Suppl.3), 70. It has now been found that a cannabinoid CB1 receptor antagonist, derived from pyrazole, selected from rimonabant and Npiperidino-5- (4-bromophenyl) 1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide has antidiabetic properties. Thus, according to the present invention, a cannabinoid CB1 receptor antagonist compound, derived from pyrazole, chosen from rimonabant and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4- ethylpyrazole-3-carboxamide, can be used for the preparation of medicaments useful for preventing and treating type 2 diabetes. The pharmaceutical compositions according to the present invention contain an effective dose of a selected pyrazole-derived cannabinoid CB1 receptor antagonist among rimonabant and Npiperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide, as well as at least one pharmaceutically acceptable excipient. Said excipients are chosen according to the pharmaceutical form and the desired mode of administration, from the usual excipients which are known to those skilled in the art. In the pharmaceutical compositions of the present invention for oral, sublingual, subcutaneous, intramuscular, intravenous, topical, local, intratracheal, intranasal, transdermal or rectal administration, the active ingredient may be administered in unit dosage form, in combination with conventional pharmaceutical excipients, animals and humans for the prevention or treatment of type 2 diabetes. Suitable unit dosage forms include oral forms such as tablets, soft or hard capsules, powders, granules and oral solutions or suspensions, sublingual, oral, intratracheal, intraocular, intranasal, inhalation, forms of topical, transdermal, subcutaneous, intramuscular or intravenous administration, forms of administration, rectal administration and implants. For topical application, the compounds according to the invention can be used in creams, gels, ointments or lotions. Forms for oral administration such as capsules or tablets are preferred. More particularly, capsules or tablets containing rimonabant are preferred at a dose of between 5 and 50 mg, more particularly at doses of 10 to 30 mg, especially the dose of 20 mg. For use according to the present invention, a cannabinoid receptor antagonist, derived from pyrazole, selected from rimonabant and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4-ethylpyrazole. 3-carboxamide may be combined with another active ingredient chosen from one of the following therapeutic classes: a lipid-lowering agent or a cholesterol-lowering agent; - another antidiabetic agent; -Another anti-obesity agent. Thus, the subject of the present invention is also pharmaceutical compositions containing in combination a cannabinoid-containing CB1 receptor antagonist, derived from pyrazole, chosen from rimonabant and N-piperidino-5- (4-bromophenyl) -1- ( 2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide, and another active ingredient selected from one of the following therapeutic classes: a lipid-lowering agent or a cholesterol-lowering agent; - another antidiabetic agent; another antiobesity agent. By lipid-lowering or cholesterol-lowering agent, is meant a compound chosen from fibrates such as alufibrate, beclobrate, bezafibrate, ciprofibrate, clinofibrate, clofibrate, etofibrate, fenofibrate; statins (HMG-CoA reductase inhibitors), such as atorvastatin, fluvastatin sodium, lovastatin, pravastatin, rosuvastatin, simvastatin, or a compound such as acipimox, aluminum nicotinate, azacosterol, cholestyramine, dextrothyroxine, meglutol, niceritrol, nicoclonate, nicotinic acid , beta-sitosterin, tiadenol. By other antidiabetic means a compound belonging to one of the following classes: sulfonylureas, biguanidines, alpha glucosidase inhibitors, thiazolidinedione, methaglinides, such as acarbose, acetohexamide, carbutamide, chlorpropamide, glibenclamide, glibornuride, gliclazide, glimepiride, glipizide, gliquidone, glisoxepide, glybuzole, glymidine, metahexamide, metformin, miglitol, nateglinide, pioglitazone, repaglinide, rosiglitazone, tolazamide, tolbutamide, voglibose. By another anti-obesity agent is meant a compound such as amfepramone, benfluorex, benzphetamine, indanorex, mazindole, mefenorex, methamphetamine, D-norpseudoephedrine, orlistat, sibutramine or other CB1 receptor antagonist to cannabinoids. According to another particular embodiment, the subject of the present invention is a pharmaceutical composition containing, in combination, rimonabant and metformin, or rimonabant and a sulphonylurea such as acetohexamide, carbutamide, c: hydropropamide, glibenclamide, glibornuride, gliclazide, glimepiride, glipizide, tolazamide, tolbutamide, for the treatment of type 2 diabetes. According to another aspect of the invention, the cannabinoid receptor antagonist, derived from pyrazole, selected from rimonabant and Npiperidino-5- (4-bromophenyl) 1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide, and the other associated active ingredient can be administered simultaneously, separately or spread over time. By "separate use" is meant the administration, at the same time, of the two compounds of the composition according to the invention, each comprised in a separate pharmaceutical form. 2882261 4 On entend par "utilisation étalée dans le temps", l'administration successive, du premier composé de la composition selon l'invention, compris dans une forme pharmaceutique, puis, du deuxième composé de la composition selon l'invention, compris dans une forme pharmaceutique distincte.  The term "use spread over time" is understood to mean the sequential administration of the first compound of the composition according to the invention, included in a pharmaceutical form, and then of the second compound of the composition according to the invention, included in a distinct pharmaceutical form. Dans le cas de cette "utilisation étalée dans le temps", le laps de temps écoulé entre l'administration du premier composé de la composition selon l'invention et l'administration du deuxième composé de la même composition selon l'invention n'excède généralement pas 24 heures, il peut être supérieur si l'un ou l'autre des composés est présenté dans un formulation phamaceutique permettant, par exemple, une administration hebdomadaire.  In the case of this "use spread over time", the lapse of time elapsed between the administration of the first compound of the composition according to the invention and the administration of the second compound of the same composition according to the invention does not exceed usually not 24 hours, it may be higher if either compound is presented in a pharmaceutical formulation allowing, for example, a weekly administration. Les formes pharmaceutiques, comprenant soit un seul des composés constitutifs de la composition selon l'invention soit l'association des deux composés, qui peuvent être mises en oeuvre dans les différents types d'utilisations décrites ci-dessus, peuvent par exemple être appropriées à l'administration orale, nasale, parentérale ou transdermique.  The pharmaceutical forms, comprising either only one of the constituent compounds of the composition according to the invention or the combination of the two compounds, which can be used in the various types of use described above, may for example be appropriate for oral, nasal, parenteral or transdermal administration. Aussi, dans le cas d'une "utilisation séparée" et d'une "utilisation étalée dans le temps", deux formes pharmaceutiques distinctes peuvent être destinées à la même voie d'administration ou à une voie d'administration différente (orale et transdermique ou orale et nasale ou parentérale et transdermique etc).  Also, in the case of "separate use" and "spread use over time", two different dosage forms may be for the same route of administration or a different route of administration (oral and transdermal). or oral and nasal or parenteral and transdermal etc). L'invention concerne donc également une trousse contenant un antagoniste des récepteurs 03 1 aux cannabinoïdes, dérivé du pyrazole, choisi parmi le rimonabant et le N-pipéridino-5-(4-bromophényl)-1-(2,4-dichlorophényl)4-éthylpyrazole-3-carboxamide, et un autre principe actif ou, le cas échéant, deux principes actifs associés dans laquelle ledit antagoniste des récepteurs CB1 aux cannabinoïdes, dérivé du pyrazole, et ledit principe actif ou, le cas échéant, deux principes actifs associés sont dans des compartiments distincts et dans des conditionnements semblables ou différents, et sont destinés à être administrés de manière simultanée, séparée ou étalée dans le temps.  The invention therefore also relates to a kit containing a pyrazole-derived cannabinoid O3 receptor antagonist, selected from rimonabant and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) 4 -ethylpyrazole-3-carboxamide, and another active ingredient or, where appropriate, two associated active ingredients in which said cannabinoid CB1 receptor antagonist, derived from pyrazole, and said active ingredient or, as the case may be, two associated active ingredients are in separate compartments and in similar or different packages, and are intended to be administered simultaneously, separately or spread over time. EXEMPLE 1: Action du rimonabant sur des patients diabétiques de type en surpoids ou obèses.  EXAMPLE 1: Action of rimonabant on overweight or obese type diabetic patients. L'étude clinique Rio-Diabete, menée pendant 12 mois chez 1045 sujets obèses présentant un diabète de type 2 traité par monothérapie (metformine ou sulfonylurées) compare l'effet du rimonabant à la dose de 20 mg versus un produit placebo dans la réduction du poids; l'amélioration de l'hémoglobine glycosylée (HbAlc), de la glycémie, de l'insulinémie ainsi que des paramètres lipidiques. Un régime alimentaire 2882261 5 hypocalorique (déficit de 600 Kcal/jour) est prescrit à tous les patients et est instauré 4 semaines avant le début de la période de traitement.  The Rio-Diabete clinical trial, conducted for 12 months in 1045 obese subjects with type 2 diabetes treated with monotherapy (metformin or sulfonylureas) compares the effect of rimonabant to the 20 mg dose versus a placebo product in the reduction of weight; improvement in glycosylated hemoglobin (HbAlc), blood glucose, insulinemia and lipid parameters. A low-calorie diet (deficit of 600 Kcal / day) is prescribed to all patients and is initiated 4 weeks before the start of the treatment period. Les sujets traités par le rimonabant à la dose de 20 mg pendant 12 mois présentent une perte de poids supérieure de 4,2 + 0,4 kg à celle observé dans le groupe placebo (p < 0,001).  Subjects treated with rimonabant 20 mg for 12 months had a greater weight loss of 4.2 + 0.4 kg compared with the placebo group (p <0.001). Sous rimonabant 20 mg, une différence de 0,7 0,1% est observée dans la réduction du taux d'HbAlc par rapport au placebo (p < 0,001). Cette diminution est maximum à 9 mois et ensuite maintenue jusqu'à 12 mois, alors que la perte de poids apparaît stabilisée après 6 mois.  Under rimonabant 20 mg, a difference of 0.7 0.1% was observed in the reduction of HbAlc compared to placebo (p <0.001). This decrease is maximum at 9 months and then maintained until 12 months, while weight loss appears stabilized after 6 months. Une baisse de la glycémie à jeun de 0,64 _1,96 mmol/L est observée dans le groupe rimonabant 20 mg, comparée à une augmentation de 0,33 2,32 mmol/L dans le groupe placebo (p < 0,001).  A decrease in fasting blood glucose of 0.64-1.96 mmol / L was observed in the rimonabant 20 mg group, compared to an increase of 0.33 2.32 mmol / L in the placebo group (p <0.001). Pour l'insulinémie à jeun on observe une diminution de 0,7 9,9 UUmL sous rimonabant 20 mg comparée à une augmentation de 0,4 14,8 UUmL dans le groupe placebo (p = 0,247).  For fasting insulinemia, a decrease of 0.7 9.9 UUmL was observed with rimonabant 20 mg compared to an increase of 0.4 14.8 UUmL in the placebo group (p = 0.247). L'insulino-résistance est évaluée par le test HOMA (de l'anglais Homeostasis Model Assessment) décrit par Matthew D.R. et al. dans Diabetologica, 1985, 28, 412-419.  Insulin resistance is evaluated by the Homeostasis Model Assessment (HOMA) test described by Matthew D.R. et al. in Diabetologica, 1985, 28, 412-419. Une amélioration de l'insulino-résistance, évaluée par le test HOMA, est objectivée sous rimonabant 20 mg (-0,5 5,7%) alors que le groupe placebo induit une détérioration de cette insulino-résistance.  An improvement of the insulin resistance, evaluated by the HOMA test, is objectified under rimonabant 20 mg (-0.5 5.7%) while the placebo group induces a deterioration of this insulin resistance. En ce qui concerne le profil lipidique, une augmentation du taux d'HDL-c supérieure de 8,4 1,2 % est observée avec le rimonabant 20 mg par rapport au placebo (p < 0,001).  Regarding the lipid profile, an increase in the HDL-c level of 8.4 ± 1.2% was observed with rimonabant 20 mg compared to placebo (p <0.001). Les triglycérides sont diminués de plus de 16,4 3,3 % dans le groupe traité par rapport au groupe placebo (p < 0,001).  Triglycerides were decreased by more than 16.4% in the treated group compared to the placebo group (p <0.001). Suite à une analyse de type régression logistique dans laquelle le poids est introduit comme une covariable, un effet indépendant de la perte de poids d'environ 55% pour l'amélioration de l'HbAlc et de l'HDL-c et d'environ 35% pour les triglycérides est observé dans cette étude.  Following a logistic regression analysis in which weight is introduced as a covariate, an effect independent of weight loss of approximately 55% for the improvement of HbAlc and HDL-c and approximately 35% for triglycerides is observed in this study. De plus, chez les patients traités par le rimonabant à la dose de 20 mg, on constate une diminution de la pression artérielle systolique de 0,8 12,8 mmHg (p=0,020) et de la pression artérielle diastolique de 1,9 8,2 mmHg (p = 0,060).  In patients treated with 20 mg rimonabant, systolic blood pressure decreased by 0.8 12.8 mmHg (p = 0.020) and diastolic blood pressure by 1.9 8 2 mmHg (p = 0.060). Ainsi chez les sujets traités par le rimonabant l'amélioration de paramètres métaboliques tels que l'HbAlc, l'HDL-c et les triglycérides n'est pas seulement liée à la perte de poids mais aussi à un effet direct du produit. 20 25  Thus in subjects treated with rimonabant the improvement of metabolic parameters such as HbAlc, HDL-c and triglycerides is not only related to weight loss but also to a direct effect of the product. 20 25 2882261 6 On constate que quelque soit le traitement antidiabétique reçu pendant l'étude, le rimonabant induit une perte de poids significative: la différence de perte de poids par rapport au groupe placebo est de 4,3 0,4 kg (p < 0,001) lors de l'association rimonabant-metformine; elle est de 3,1 0,5 kg (p < 0,001) lors de l'association rimonabantsulfonylurée.  2882261 6 It is observed that whatever the antidiabetic treatment received during the study, rimonabant induces a significant weight loss: the difference in weight loss compared to the placebo group is 4.3 0.4 kg (p <0.001) during rimonabant-metformin combination; it is 3.1 0.5 kg (p <0.001) when rimonabantsulfonylurea is combined. On constate également que les résultats sur l'HbAlc sont similaires avec une différence observée par rapport au placebo de 0,7 0, 1% (p<0,001) que le rimonabant soit en association avec la metformine ou avec une sulfonylurée EXEMPLE 6: Composition pharmaceutique.  It is also noted that the results on HbAlc are similar with an observed difference compared to placebo of 0.7 0, 1% (p <0.001) that rimonabant is in combination with metformin or with a sulfonylurea EXAMPLE 6: Composition pharmaceutical. 0 Pour l'administration aux patients, le rimonabant est formulé dans des compositions pharmaceutiques qui sont préparées par granulation humide. CONSTITUANTS Rimnonabant micronisé 20,0 mg Amidon de maïs 67,50 mg Lactose monohydrate 111,66 mg Povidone * 5,25 mg Croscarmellose de sodium 18,75 mg Laurylsulfate de sodium 0,34 mg Cellulose microcristalline 75,0 mg Stéarate de magnésium 1,50 mg Comprimé terminé à 300 mg * La Povidone est définie dans la Pharmacopée Européenne comme suit: poly(l-(2-oxo-lpyrrolidinyl)éthylène) et est constituée de polymères linéaires de 1vinylpyrrolidin-É2-one.  For administration to patients, rimonabant is formulated into pharmaceutical compositions which are prepared by wet granulation. CONSTITUENTS Micronized Rimoniabant 20.0 mg Corn Starch 67.50 mg Lactose Monohydrate 111.66 mg Povidone * 5.25 mg Croscarmellose Sodium 18.75 mg Sodium Lauryl Sulfate 0.34 mg Microcrystalline Cellulose 75.0 mg Magnesium Stearate 1 , 50 mg Tablet finished at 300 mg * Povidone is defined in the European Pharmacopoeia as follows: poly (1- (2-oxo-1-pyrrolidinyl) ethylene) and consists of linear polymers of 1-vinylpyrrolidin-2-one. Les comprimés sont préférentiellement enrobés en utilisant un excipient approprié.  The tablets are preferably coated using a suitable excipient. 7 REVENDICATIONS 1. 2. 3. 4. 5. 6. 7.  7 1. 2. 3. 4. 5. 6. 7. Utilisation d'un composé antagoniste des récepteurs CB1 aux cannabinoïdes choisi parmi le rimonabant et le N-pipéridino-5-(4-bromophényl)-1-(2,4dichlorophényl)-4-éthylpyrazole-3-carboxamide, pour la préparation de médicaments utiles dans le traitement et la prévention du diabète de type 2. Utilisation selon la revendication 1 dans laquelle l'antagoniste des récepteurs CB1 aux cannabinoïdes est associé à un autre principe actif choisi parmi l'une des classes thérapeutiques suivantes: -un hypolipémiant ou un hypocholestérolémiant; - un antidiabétique; - un autre agent anti-obésité.  Use of a cannabinoid CB1 receptor antagonist compound selected from rimonabant and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide for the preparation of medicaments useful in the treatment and prevention of type 2 diabetes. Use according to claim 1 wherein the cannabinoid CB1 receptor antagonist is associated with another active ingredient selected from one of the following therapeutic classes: a lipid-lowering agent or a cholesterol; - an antidiabetic; another anti-obesity agent. Utilisation selon l'une quelconque des revendications 1 ou 2 dans laquelle le composé antagoniste des récepteurs CB1 aux cannabinoïdes est le rimonabant. Utilisation selon la revendication 3 dans laquelle le rimonabant est utilisé à une dose comprise entre 5 mg et 50 mg.  Use according to any one of claims 1 or 2 wherein the cannabinoid CB1 receptor antagonist compound is rimonabant. Use according to claim 3 wherein the rimonabant is used at a dose of between 5 mg and 50 mg. Utilisation selon la revendication 4 dans laquelle le rimonabant est associé à la metformine.  Use according to claim 4 wherein the rimonabant is associated with metformin. Utilisation selon la revendication 4 dans laquelle le rimonabant est associé à une sulfonylurée.  Use according to claim 4 wherein the rimonabant is associated with a sulfonylurea. Composition pharmaceutique contenant en association un composé antagoniste des récepteurs CB1 aux cannabinoïdes choisi parmi le rimonabant et le N-pipéridino-5-(4-bromophényl)-1-(2,4-dichlorophényl)-4- éthylpyrazole-3 carboxamide et un autre principe actif choisi parmi la metformine, une sulfonylurée.  A pharmaceutical composition comprising in combination a cannabinoid CB1 receptor antagonist compound selected from rimonabant and N-piperidino-5- (4-bromophenyl) -1- (2,4-dichlorophenyl) -4-ethylpyrazole-3-carboxamide and another active ingredient selected from metformin, a sulfonylurea.
FR0501861A 2005-02-21 2005-02-21 USE OF A PYRAZOLE DERIVATIVE FOR THE PREPARATION OF MEDICAMENTS USEFUL IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES Expired - Fee Related FR2882261B1 (en)

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FR0501861A FR2882261B1 (en) 2005-02-21 2005-02-21 USE OF A PYRAZOLE DERIVATIVE FOR THE PREPARATION OF MEDICAMENTS USEFUL IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES
FR0504942A FR2882264A1 (en) 2005-02-21 2005-05-12 Use of rimonabant and N-peperidino-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide, having cannabinoids receptor antagonistic activity, to treat and prevent type-II diabetes
FR0505228A FR2882265B1 (en) 2005-02-21 2005-05-23 USE OF A PYRAZOLE DERIVATIVE FOR THE PREPARATION OF MEDICAMENTS USEFUL IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES.
BRPI0608183-5A BRPI0608183A2 (en) 2005-02-21 2006-02-20 use of rimonabant for the preparation of drugs useful in the prevention and treatment of type 2 diabetes
PCT/FR2006/000376 WO2006087481A1 (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
JP2007555669A JP2008530189A (en) 2005-02-21 2006-02-20 Use of rimonabant to prepare a medicament that can be used in the prevention and treatment of type 2 diabetes
MX2007009996A MX2007009996A (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes.
UY29386A UY29386A1 (en) 2005-02-21 2006-02-20 USE OF RIMONABANT FOR THE PREPARATION OF USEFUL MEDICINES IN THE PREVENTION AND TREATMENT OF TYPE2 DIABETES.
CA002597245A CA2597245A1 (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
CNA2006800052531A CN101119727A (en) 2005-02-21 2006-02-20 Application of rimonabant in preparing medicine for preventing and treating type 2 diabetes
TW095105631A TW200640457A (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments useful in the prevention and treatment of type 2 diabetes
ZA200707012A ZA200707012B (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
AU2006215444A AU2006215444A1 (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
EA200701781A EA011618B1 (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
KR1020077018993A KR20070104913A (en) 2005-02-21 2006-02-20 Use of Rimonabant for the manufacture of a medicament that can be used for the prevention and treatment of type 2 diabetes
EP06709344A EP1853264A1 (en) 2005-02-21 2006-02-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
ARP060100611A AR053812A1 (en) 2005-02-21 2006-02-21 USE OF RIMONABANT FOR THE PREPARATION OF USEFUL DRUGS IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES
TNP2007000297A TNSN07297A1 (en) 2005-02-21 2007-07-31 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
US11/832,865 US20080015229A1 (en) 2005-02-21 2007-08-02 Use of rimonabant for the preparation of medicaments useful in the prevention and treatment of type 2 diabetes
CR9293A CR9293A (en) 2005-02-21 2007-08-07 USE OF RIMONABANT FOR THE PREPARATION OF USEFUL DRUGS IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES
IL185401A IL185401A0 (en) 2005-02-21 2007-08-20 Use of rimonabant for the preparation of medicaments that can be used in the prevention and treatment of type 2 diabetes
MA30158A MA29262B1 (en) 2005-02-21 2007-08-23 USE OF RIMONABANT FOR THE PREPARATION OF MEDICAMENTS USEFUL IN THE PREVENTION AND TREATMENT OF TYPE 2 DIABETES
NO20074767A NO20074767L (en) 2005-02-21 2007-09-18 Use of rimonabant for the preparation of drugs that can be used in the prevention and treatment of type 2 diabetes
US12/402,988 US20090197917A1 (en) 2005-02-21 2009-03-12 Use of rimonabant for the preparation of medicaments useful in the prevention and treatment of type 2 diabetes

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