Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
  • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• • 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
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic 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
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/445—Non condensed piperidines, e.g. piperocaine
• • 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
• • 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
  • A61P3/06—Antihyperlipidemics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P9/00—Drugs for disorders of the cardiovascular system
  • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

• EP 1 117 645 discloses propanolamine derivatives with a hypolipidemic effect.
• the invention was based on the object of providing mixtures of substances or combination preparations of propanolamine derivatives of the formula I with further active compounds which have a synergistic effect.
• the hypolipidemic effect of the propanolamine derivatives of the formula I in the combination preparations should be disproportionately increased by the synergistic effect with other active ingredients.
• the invention therefore relates to mixtures of propanolamine derivatives of the formula I,
• Fluorine can be replaced and where phenyl and pyridyl in turn can be simply substituted by methyl, methoxy or halogen;
• R 2 H OH, CH 2 OH, OMe, CHO, NH 2 ;
• Sugar residue, sugar residue, tri-sugar residue or tetra-sugar residue is optionally substituted one or more times by one of the sugar protecting groups, HO-SO 2 -, (HO) 2 -PO-;
• R 4 H methyl, F, OMe
• R 9 to R 12 independently of one another are H, d-C ⁇ -alkyl
• R 1 phenyl, thiazolyl, oxazolyl, isoxazolyl, where the aromatic or
• Heteroaromatic can be substituted one to two times with fluorine, chlorine, bromine, (C C ⁇ ) -alkyl;
• sugar residue is optionally substituted one or more times by one of the sugar protecting groups, HO-SO 2 -;
• R 4 H methyl, F, OMe
• heteroatoms in particular include, for example O, S, N into consideration.
• the heteroaromatic rings have 1-15 C atoms and 1-6 heteroatoms, preferably 1-5 C atoms and 1-2 heteroatoms.
• Thiophene, furan, pyridine, pyrimidine, indole, quinoline, oxazole, isoxazole, thiazole or isothiazole are suitable for the heteroaryl groups mentioned in the preceding definitions.
• alkyl means straight-chain or branched hydrocarbon chains.
• Sugar residues are understood to mean compounds which are derived from aldoses and ketoses having 3 to 7 carbon atoms and which can belong to the D or L series; this also includes amino sugar, sugar alcohols or sugar acids. Examples include glucose, mannose, fructose, galactose, ribose, erythrose, glyceraldehyde, sedoheptulose, glucosamine, galactosamine, glucuronic acid, galacturonic acid, gluconic acid, galactonic acid, mannonic acid, glucamine, 3-amino-1, 2-propanediol, glucaric acid and galactaric acid.
• Dizucker means saccharides that consist of two sugar units. Di-, tri-, or tetrasaccharides are formed by acetal-like binding of two or more sugars. The bonds can occur in the ⁇ or ß form. Lactose, maltose and cellobiose may be mentioned as examples.
• the substitution is preferably carried out on the hydrogen atom of an OH group of the sugar.
• the following protective groups are essentially suitable for the hydroxyl groups of the sugars: benzyl, acetyl, benzoyl, pivaloyl, trityl, tert-butyldimethylsilyl, benzylidene, cyclohexylidene or isopropylidene protective groups.
• amino acids or amino acid residues are the stereoisomeric forms, i.e. D or L forms, meaning the following compounds:
• Piperidic acid 2,2-diaminopimelic acid 6-aminocaproic acid 2,3-diaminopropionic acid
• amino protective groups suitable are groups with which the functional groups of the side chains of amino acid residues are protected (see, eg. TW Greene, PGM Wuts, Protective Groups in Organic Synthesis, 2 ⁇ d Edition, John Wiley and Sons, New York 1991). Mainly used: t-butyloxy-carbonyl (BOC), 9-fluorenylmethoxy-carbonyl (Fmoc), benzyloxy-carbonyl (Z), 2- (3,5-dimethoxyphenyl) prop-2-yloxycarbonyl (Ddz), methyl, t - butyl, trityl, st-butyl.
• BOC t-butyloxy-carbonyl
• Fmoc 9-fluorenylmethoxy-carbonyl
• Z benzyloxy-carbonyl
• Ddz 2- (3,5-dimethoxyphenyl) prop-2-yloxycarbonyl
• Suitable pharmaceutically acceptable acid addition salts of the compounds according to the invention are salts of inorganic acids, such as hydrochloric acid, hydrobromic, phosphoric, metaphosphoric, nitric, sulfamic and sulfuric acid, and organic acids, such as e.g.
• the chloride salt is used in a particularly preferred manner for medical purposes.
• Suitable pharmaceutically acceptable basic salts are ammonium salts, alkali metal salts (such as sodium and potassium salts) and alkaline earth metal salts (such as magnesium and calcium salts).
• Salts with a non-pharmaceutically acceptable anion also belong in the Framework of the invention as useful intermediates for the production or purification of pharmaceutically acceptable salts and / or for use in non-therapeutic, for example in vitro, applications.
• physiologically functional derivative denotes any physiologically compatible derivative of a compound of formula I according to the invention, e.g. an ester which, when administered to a mammal, e.g. humans, is able to (directly or indirectly) form a compound of formula I or an active metabolite thereof.
• the physiologically functional derivatives also include prodrugs of the compounds according to the invention.
• prodrugs can be metabolized in vivo to a compound according to the invention. These prodrugs may or may not be effective themselves.
• the amount of a compound of the formula (I) and of further active ingredients which are required to achieve the desired biological effect with the combination depends on a number of factors, for example the specific compound chosen, the intended use, the type of Administration and clinical condition of the patient.
• the daily dose is in the range from 0.1 mg to 100 mg (typically from 0.1 mg to 50 mg) per day per kilogram of body weight, for example 0.1-10 mg / kg / day.
• Tablets or capsules can contain, for example, from 0.01 to 100 mg, typically from 0.02 to 50 mg.
• the aforementioned weight data relate to the weight of the aminopropanol ion derived from the salt.
• the substance mixtures are preferably in the form of a pharmaceutical composition with a compatible carrier.
• the carrier must of course be compatible, in the sense that it is compatible with the other components of the composition and is not harmful to the health of the patient.
• the carrier can be a solid or a liquid or both and is preferably formulated with the compounds as a single dose, for example as a tablet, which can contain from 0.05% to 95% by weight of the active ingredient.
• Other pharmaceutically active substances can also be present, including other compounds of formula (I).
• the pharmaceutical compositions according to the invention can be prepared by one of the known pharmaceutical methods, which consist essentially in the fact that the constituents are mixed with pharmacologically acceptable carriers and / or auxiliaries.
• compositions according to the invention are those which are suitable for oral and peroral (eg sublingual) administration, although the most suitable mode of administration in each individual case depends on the type and severity of the condition to be treated and on the type of the compound of formula (I) used in each case , Coated formulations and coated slow-release formulations also fall within the scope of the invention.
• Formulations which are resistant to acid and gastric juice are preferred.
• Suitable enteric coatings include cellulose acetate phthalate, polyvinyl acetate phthalate, hydroxypropylmethyl cellulose phthalate and anionic polymers of methacrylic acid and methyl methacrylate.
• Suitable pharmaceutical compounds for oral administration can be present in separate units, such as capsules, capsules, lozenges or tablets, each of which contains a certain amount of the compound of the formula (I) and the further active ingredient; as powder or granules; as a solution or suspension in an aqueous or non-aqueous liquid; or as an oil-in-water or water-in-oil emulsion.
• these compositions can be prepared by any suitable pharmaceutical method which comprises a step in which the active ingredient and the carrier (which may consist of one or more additional ingredients) are brought into contact.
• the compositions are prepared by uniformly and homogeneously mixing the active ingredient with a liquid and / or finely divided solid carrier, after which the product is shaped if necessary.
• a tablet can be made by compressing or molding a powder or granules of the compound, optionally with one or more additional ingredients.
• Pressed tablets can be prepared by tabletting the compound in free-flowing form, such as a powder or granules, optionally mixed with a binder, lubricant, inert diluent and / or a (several) surface-active / dispersing agent in a suitable machine.
• Molded tablets can be made by molding the powdered compound moistened with an inert liquid diluent in a suitable machine.
• compositions suitable for oral (sublingual) administration include lozenges containing a compound of formula (I) and the other active ingredient with a flavoring agent, usually sucrose and gum arabic or tragacanth, and lozenges containing the compound in one include inert bases such as gelatin and glycerin or sucrose and acacia.
• active ingredients for the combination preparations are also suitable as active ingredients for the combination preparations: all antidiabetic agents mentioned in the 2001 Red List, Chapter 12. They can be combined with the compounds of the formula I according to the invention in particular to improve the synergistic effect.
• the active ingredient combination can be administered either by separate administration of the active ingredients to the patient or in the form of combination preparations in which several active ingredients are present in a pharmaceutical preparation. Most of the active ingredients listed below are disclosed in the USP Dictionary of USAN and International Drug Names, US Pharmacopeia, Rockville 2001.
• Antidiabetics include insulin and insulin derivatives, such as Lantus ® (see www.lantus.com) or HMR 1964 fast-acting insulins (see US 6,221, 633), GLP-1 derivatives such as those described in WO 98/08871 of Novo Nordisk A / S have been disclosed, as well as orally active hypoglycemic agents.
• the orally active hypoglycemic agents preferably include sulphonylureas, biguanides, meglitinides, oxadiazolidinediones, thiazolidinediones, glucosidase inhibitors, glucagon antagonists, GLP-1 agonists, potassium channel openers, such as those described in WO 97/26265 and WO 99/03861 Novo Nordisk A / S, insulin sensitizers, inhibitors of liver enzymes involved in stimulating gluconeogenesis and / or glycogenolysis, modulators of glucose uptake, lipid-modifying compounds such as antihyperlipidemic agents and antilipidemic agents, 5 compounds that increase food intake decrease, PPAR and PXR agonists and agents that act on the ATP-dependent potassium channel of beta cells.
• sulphonylureas biguanides, meglitinides, oxadiazolidinediones, thiazolidinediones, glucosidas
• the compounds of the formula I are used in combination with an HMG-CoA reductase inhibitor, such as simvastatin, fluvastatin,
• PPAR gamma agonist e.g. Rosiglitazone, pioglitazone, JTT-
• the compounds of the formula I in combination with PPAR alpha agonist e.g. GW 9578, GW 7647.
• the compounds of the formula I are used in combination with a mixed PPAR alpha / gamma agonist, e.g. GW 25 1536, AVE 8042, AVE 8134, AVE 0847, or as described in PCT / US00 / 11833, PCT / US00 / 11490, DE10142734.4.
• a mixed PPAR alpha / gamma agonist e.g. GW 25 1536, AVE 8042, AVE 8134, AVE 0847, or as described in PCT / US00 / 11833, PCT / US00 / 11490, DE10142734.4.
• the compounds of the formula I in combination with a fibrate such as e.g. Fenofibrate, clofibrate, bezafibrate.
• the compounds of the formula I are used in combination with an MTP inhibitor, such as, for example, Implitapide, BMS-201038, R-103757, administered.
• an MTP inhibitor such as, for example, Implitapide, BMS-201038, R-103757, administered.
• the compounds of the formula I are used in combination with bile acid absorption inhibitor (see, for example, US 6,245,744 or US 6,221, 897), such as e.g. HMR 1741.
• the compounds of the formula I in combination with a CETP inhibitor such as e.g. JTT-705.
• the compounds of Formet I in combination with a polymeric bile acid adsorber such as e.g. Cholestyramine, Colesevelam.
• the compounds of the formula I are used in combination with an LDL receptor inducer (see US 6,342,512), e.g. HMR1171, HMR1586.
• the compounds of the formula I in combination with an ACAT inhibitor such as e.g. Avasimibe administered.
• the compounds of the formula I in combination with an antioxidant, such as e.g. OPC-14117.
• the compounds of the formula I are used in combination with a lipoprotein lipase inhibitor, e.g. NO-1886.
• the compounds of the formula I are used in combination with an ATP citrate lyase inhibitor, e.g. SB-204990.
• the compounds of the formula I are administered in combination with a squalene synthetase inhibitor, such as, for example, BMS-188494. In one embodiment of the invention, the compounds of the formula I are administered in combination with a lipoprotein (a) antagonist, such as, for example, CI-1027 or nicotinic acid.
• a squalene synthetase inhibitor such as, for example, BMS-188494.
• a lipoprotein (a) antagonist such as, for example, CI-1027 or nicotinic acid.
• the compounds of the formula I in combination with a lipase inhibitor, such as e.g. Orlistat administered.
• a lipase inhibitor such as e.g. Orlistat administered.
• the compounds of the formula I are administered in combination with insulin.
• the compounds of the formula I are used in combination with a sulphonyl urea, e.g. Tolbutamide, glibenclamide, glipizide or glimepiride administered.
• a sulphonyl urea e.g. Tolbutamide, glibenclamide, glipizide or glimepiride administered.
• the compounds of formula I in combination with a biguanide e.g. Metformin.
• the compounds of formula I in combination with a thiazolidinedione such as e.g. Troglitazone, ciglitazone, pioglitazone, rosiglitazone or those described in WO 97/41097 by Dr. Reddy's Research Foundation disclosed compounds, in particular 5 - [[4 - [(3,4-dihydro-3-methyl-4-oxo-2-quinazolinyl-methoxy] phenyl] methyl] -2,4-thiazolidinedione
• the compounds of the formula I are administered in combination with a ⁇ -glucosidase inhibitor, such as, for example, miglitol or acarbose.
• the compounds of the formula I are administered in combination with an active ingredient which acts on the ATP-dependent potassium channel of the beta cells, such as, for example, tolbutamide, glibenclamide, glipizide, glimepiride or repaglinide.
• the compounds of the formula I are used in combination with more than one of the abovementioned compounds, for example in combination with a sulphonylurea and metformin, a sulphonylurea and acarbose, repaglinide and metformin, insulin and a sulphonylurea, insulin and Metformin, insulin and troglitazone, insulin and lovastatin, etc. administered.
• the compounds of the formula I are used in combination with CART modulators (see “Cocaine-amphetamine-regulated transcript influences energy metabolism, anxiety and gastric emptying in mice” Asakawa, A, et al., M.:Hormone and Metabolie Research (2001), 33 (9), 554-558), NPY antagonists e.g. Naphthalene-1-sulfonic acid ⁇ 4 - [(4-amino-quinazolin-2-ylamino) methylj-cyclohexyl methyl ⁇ amide; hydrochloride (CGP 71683A)), MC4 agonists (e.g.
• CRF BP antagonists e.g. urocortin
• urocortin agonists e.g. 1- (4-chloro-3-methanesulfonylmethylphenyl) -2- [2- (2,3-dimethyl- 1 H-indol-6-yloxy) ethylaminoj-ethanol; hydrochloride (WO 01/83451)
• MSH melanocyte-stimulating hormone
• CCK-A agonists e.g.
• Trifluoroacetic acid salt (WO 99/15525)); Serotonin reuptake inhibitors (e.g. dexfenfluramines), mixed serotonin and noradrenergic compounds (e.g. WO 00/71549), 5HT agonists e.g. 1- (3-ethyl-benzofuran-7-yl) piperazine oxalic acid salt (WO 01/09111) , Bombesin agonists, galanin antagonists, growth hormone (e.g.
• growth hormone human growth hormone
• growth hormone releasing compounds (6-benzyloxy-1- (2-diisopropylamino-ethylcarbamoyl) -3,4-dihydro-1 H-isoquinoline-2-carboxylic acid aeid tert -butyl ester (WO 01/85695)
• TRH agonists see, for example, EP 0 462 884
• decoupling protein 2 or 3 modulators leptin agonists
• leptin agonists see, for example, Lee, Daniel W .; Leinung, Matthew C; Rozhavskaya-Arena, Marina; Grasso, Patricia. Leptin agonists as a potential approach to the treatment of obesity.
• Drugs of the Future (2001), 26 (9), 873-881), DA agonists (bromocriptine, doprexin), lipase / amylase- Inhibitors (e.g. WO 00/40569), PPAR modulators (for example WO 00/78312), RXR modulators or TR - agonists.
• DA agonists bromocriptine, doprexin
• lipase / amylase- Inhibitors e.g. WO 00/40569
• PPAR modulators for example WO 00/78312
• RXR modulators or TR - agonists e.g. WO 00/78312
• the further active ingredient is leptin, see e.g. "Perspectives in the therapeutic use of leptin", Salvador, Javier; Gomez-Ambrosi, Javier; Fruhbeck, Gema, Expert Opinion on Pharmacotherapy (2001), 2 (10), 1615-1622.
• the further active ingredient is dexamphetamine or amphetamine.
• the further active ingredient is fenfluramine or dexfenfluramine.
• the further active ingredient is sibutramine.
• the further active ingredient is orlistat.
• the further active ingredient is mazindol or phentermine.
• the compounds of formula I in combination with bulking agents preferably insoluble bulking agents
• bulking agents preferably insoluble bulking agents
• Caromax is a carob-containing product from Nutrinova, Nutrition Specialties & Food Ingredients GmbH, Industriepark availability, 65926 Frankfurt / Main)).
• the combination with Caromax ® can be carried out in one preparation or by separate administration of compounds of the formula I and Caromax ® .
• Caromax ® can also be administered in the form of food, such as in baked goods or granola bars.
• the combination of compounds of formula I with Caromax ® is characterized not only by an improvement in activity, in particular in the lowering of LDL cholesterol, compared to the individual active substances, but also by their improved tolerance.
• the combination preparations or substance mixtures of the compounds of the formula I represent ideal medicaments for the treatment of lipid metabolism disorders and / or carbohydrate metabolism disorders, in particular hyperlipidemia and metabolic syndrome.
• the combination preparations are also suitable for influencing the serum cholesterol level as well as for the prevention and treatment of arteriosclerotic symptoms.
• Rectal drug form containing 40 mg active substances per suppository: 40 mg active substances per suppository
• Example E coated tablets containing 50 mg active ingredients per coated tablet: per coated tablet
• Example F The following recipes are suitable for producing the contents of hard gelatin capsules: a) Active ingredients 100 mg corn starch 300 mg
• Drops can be prepared according to the following recipe (100 mg active ingredient in 1 ml
• mice Male Syrian hamsters (Mesocricetus auratus) aged 8 to 10 weeks were used for the experiment. The animals received a standard feed enriched with 0.1% cholesterol (Fa Teklad 8604M). An additional normal control group received only standard feed.
• test substances were treated orally with a pharyngeal tube once a day for 12 consecutive days, the control group was treated with the vehicle.
• the faeces were collected for bile acid analysis.
• blood was taken retroorbitally from the animals and the lipid levels in the plasma were determined.
• Oral radioactive tracers were administered to the animals on experiment day 11, to determine the cholesterol absorption according to the method described by Zilversmith et al. described method.
• day 13 of the experiment the animals were sacrificed and the animals' livers were removed for cholesterol analysis and microsome preparation. The activity of the 7 ⁇ -hydroxylase was determined ex vivo in the liver microsomes using a modified method by Hylemon et al.
• connection V1 with Caromax® Preparation mg / 200 ml
• Test animals Male Syrian hamster (Mesocricetus auratus) from Harlan 80-100 g at the beginning of the adaptation
• liver weight Liver cholesterol 1x500mg in EtOH / KOH (sample is also used for CH synthesis)
• CYP7 activity live microsomes as a group pool, 0.5 g each - preparation on the day of the experiment
• 5% Caromax 5% Caromax added to the feed; corresponds to a dose of 5000mg / kg / day
• Ezetimibe (KOO 04513) is a cholesterol absorption inhibitor from Schering Plow
• Test animals Male Syrian hamster (Mesocricetus auratus) from Harlan
• CYP7 activity live microsomes as a group pool, 0.5 g each - preparation on
• the manure is then dried and burned in the Oximat (Packard) to determine the isotope
• K 00 04513 Ezetimibe cholesterol absorption inhibitor
• treatment with 0.1 mg / kg K 00 04513 lowers the LDL cholesterol to 94% and treatment mg / kg V1 (line 6) lowers the LDL cholesterol to 87%.
• treatment with 0.1 mg / kg K 00 045 13 and 3 mg / kg V1 lowers the LDL cholesterol to 28%.

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