CA1041013A - Appetite curbing preparation containing an alginate and a diphosphonic acid - Google Patents
Appetite curbing preparation containing an alginate and a diphosphonic acidInfo
- Publication number
- CA1041013A CA1041013A CA221,248A CA221248A CA1041013A CA 1041013 A CA1041013 A CA 1041013A CA 221248 A CA221248 A CA 221248A CA 1041013 A CA1041013 A CA 1041013A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- alginic
- compound
- appetite
- curbing
- 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.)
- Expired
Links
- 230000036528 appetite Effects 0.000 title claims abstract description 26
- 235000019789 appetite Nutrition 0.000 title claims abstract description 26
- 235000010443 alginic acid Nutrition 0.000 title claims abstract description 8
- 229920000615 alginic acid Polymers 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 22
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 title abstract description 5
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 title abstract description 3
- 229940072056 alginate Drugs 0.000 title abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 241001465754 Metazoa Species 0.000 claims abstract description 13
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 13
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 24
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000000783 alginic acid Substances 0.000 claims description 5
- 229960001126 alginic acid Drugs 0.000 claims description 5
- 150000004781 alginic acids Chemical class 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 230000036961 partial effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- LDTZSTJLVYBEKB-UHFFFAOYSA-N butedronic acid Chemical class OC(=O)CC(C(O)=O)C(P(O)(O)=O)P(O)(O)=O LDTZSTJLVYBEKB-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 18
- 239000003112 inhibitor Substances 0.000 abstract description 17
- 159000000007 calcium salts Chemical class 0.000 abstract description 5
- 238000001879 gelation Methods 0.000 description 14
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 9
- 229910001424 calcium ion Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 5
- 235000010413 sodium alginate Nutrition 0.000 description 5
- 239000000661 sodium alginate Substances 0.000 description 5
- 229940005550 sodium alginate Drugs 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 230000000578 anorexic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003352 sequestering agent Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000010410 calcium alginate Nutrition 0.000 description 2
- 239000000648 calcium alginate Substances 0.000 description 2
- 229960002681 calcium alginate Drugs 0.000 description 2
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- SXGRAKNNKBAFML-UHFFFAOYSA-N 1,3-diphosphonopropan-2-ylphosphonic acid Chemical compound OP(O)(=O)CC(P(O)(O)=O)CP(O)(O)=O SXGRAKNNKBAFML-UHFFFAOYSA-N 0.000 description 1
- GAPYCUKJBQZFAZ-UHFFFAOYSA-N 2-(1,1-diphosphonoethyl)butanedioic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(C)C(C(O)=O)CC(O)=O GAPYCUKJBQZFAZ-UHFFFAOYSA-N 0.000 description 1
- INJFRROOFQOUGJ-UHFFFAOYSA-N 2-[hydroxy(methoxy)phosphoryl]butanedioic acid Chemical compound COP(O)(=O)C(C(O)=O)CC(O)=O INJFRROOFQOUGJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- YJNBCJLDSPNBOH-UHFFFAOYSA-N [[carboxy(hydroxy)phosphoryl]oxy-hydroxyphosphoryl]formic acid Chemical class OC(=O)P(O)(=O)OP(O)(=O)C(O)=O YJNBCJLDSPNBOH-UHFFFAOYSA-N 0.000 description 1
- BFDMEODWJJUORJ-UHFFFAOYSA-N [dimethylamino(phosphono)methyl]phosphonic acid Chemical compound CN(C)C(P(O)(O)=O)P(O)(O)=O BFDMEODWJJUORJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000010407 ammonium alginate Nutrition 0.000 description 1
- 239000000728 ammonium alginate Substances 0.000 description 1
- KPGABFJTMYCRHJ-YZOKENDUSA-N ammonium alginate Chemical compound [NH4+].[NH4+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O KPGABFJTMYCRHJ-YZOKENDUSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PZVXRVSZEYPTCG-UHFFFAOYSA-N benzyl-[chloro(hydroxy)phosphoryl]oxyphosphinic acid Chemical compound ClP(OP(=O)(O)CC1=CC=CC=C1)(=O)O PZVXRVSZEYPTCG-UHFFFAOYSA-N 0.000 description 1
- NRIMHVFWRMABGJ-UHFFFAOYSA-N bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid Chemical compound C1C2C(C(=O)O)=C(C(O)=O)C1C=C2 NRIMHVFWRMABGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DLEPCXYNAPUMDZ-UHFFFAOYSA-N butan-2-ylphosphonic acid Chemical compound CCC(C)P(O)(O)=O DLEPCXYNAPUMDZ-UHFFFAOYSA-N 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- NHWZQIYTQZEOSJ-UHFFFAOYSA-N carbonic acid;phosphoric acid Chemical compound OC(O)=O.OP(O)(O)=O NHWZQIYTQZEOSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WLWKIJKUDWYINL-UHFFFAOYSA-N cyclohexane-1,1,2,2,3,3-hexacarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC(C(O)=O)(C(O)=O)C1(C(O)=O)C(O)=O WLWKIJKUDWYINL-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000001916 dieting Nutrition 0.000 description 1
- 230000037228 dieting effect Effects 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000010408 potassium alginate Nutrition 0.000 description 1
- 239000000737 potassium alginate Substances 0.000 description 1
- MZYRDLHIWXQJCQ-YZOKENDUSA-L potassium alginate Chemical compound [K+].[K+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O MZYRDLHIWXQJCQ-YZOKENDUSA-L 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/256—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seaweeds, e.g. alginates, agar or carrageenan
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Non-Alcoholic Beverages (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
An appetite curbing preparation comprising an alginate and diphosphonic acid or a nontoxic pharma-cologically acceptable water-soluble salt thereof as an inhibitor of the precipitation of calcium salts. This preparation is useful for curbing the appetite of a warm-blooded animal.
An appetite curbing preparation comprising an alginate and diphosphonic acid or a nontoxic pharma-cologically acceptable water-soluble salt thereof as an inhibitor of the precipitation of calcium salts. This preparation is useful for curbing the appetite of a warm-blooded animal.
Description
1(~4101~
The present invention relates to appetite curbing compositions for mammals, methods for the preparation of such compositions, and methods for curbing the appetite of mammals by use of said compositions.
It is known to produce preparations based on alignates for use as appetite curbing agents in slimming diets. Since these preparations swell in the stomach and ~ `
intestinal tract, they produce a feeling of fullness and satisfaction in human beings. However, the preparations 10 have a considerable disadvantage in that in the presence of calcium ions they form calcium-containing deposits of low solubility. As a result, it is possible for a calcium ion deficiency to be produced, particularly in the intestinal tract. The fear has therefore often been voiced that dis-turbances of the metabolism could thereby be produced.
It is an object of the present invention to over-come the above-described drawbacks of the prior art.
It is another object of the present invention to proyide A preparation comprising alginic acid and a diphosphonic 20 acid ~or nontoxic pharmacologically acceptable water-soluble salts thereof~ in which the diphosphonic- acid acts as inhibitor of the precipitation of calcium salts; and thereby inhibits precipitation of calcium ions; this preparation is useful for curbing the appetite of a warm-blooded animal.
These and further objects of the present invention -~
will become apparent as the description thereof proceeds.
The present invention relates to alginic acid pre-parations containing a diphosphonic acid (or nontoxic pharma-cologically acceptable water-soluble salts thereof) as inhibitor 30 of the precipitation of calcium salts when the composition is ingested. This preparation is useful as an appetite curbing agent for warm-blooded animals.
cb/ - 1 -1(~410~3 Accordingly, the present invention provides a pre-paration for use in curbing the appetite of warm-blooded animals which comprises an alginic compound and a diphosphonic compound of the formula:
wherein Rl is hydrogen or methyl and the nontoxic pharma-cologically acceptable water-soluble salts thereof, as inhibitor of the precipitation of calcium salts when the composition is administered to warm-blooded animals.
More particularly, the present invention is directed to an appetite curbing preparation for warm-blooded animals comprising (A) an alginic compound selected from the groups consisting of alginic acid and the nontoxic pharmacologically acceptable water-soluble salts thereof, and ~ 3) a substoichiometric amount based on the calcium ions required to gel said ~lginic compound of a diphosphonic compound as precipitation inhibitor for calcium ions selected ; from the group consisting of a diphosphonic compound having the formula CH2 ~ IH ~ I R
wherein Rl is hydrogen or methyl and the nontoxic pharma-cologically acceptable water-soluble salts thereof.
Also, the present invention provides an appetite curbing composition for a warm-blooded animal consisting essen-tially of 25% to 50% by weight of the above appetite curbingpreparation and 50~ to 75% by weight of a nontoxic pharma-~ologically acceptable carrier.
,,,, ~
~- cb/ - 2 -In addition, the present invention provides a method for curbing the appetite of warm-blooded animals comprising ~ :
administering to said animals an anoretically effective amount of the appetite curbing preparation mentioned above.
Also, the present invention provides an improvement in a process for dieting, which consists essentially in con-suming ~during or before a meal) an effective amount of the appetite curbing preparation mentioned above as an anoretic material.
It has become apparent that in principle it is possible to preyent the formation of calcium alginate by add-ing thereto a strong sequestering agent, for example, nitrilo-triacetic acid or ethylenediaminetetraacetic acid. However, the calcium ions are thereby sequestered to such an extent that they may possibly no longer be available for physiological processes in the warm-blooded animal. Moreover, the precipi-tation of the calcium salts can be prevented for a consider-able period of time by using compounds which have a strong -~
inhibiting effect (threshold effect). In this case, crystalline growth is probably inhibited to a very great extent by the incorporation of the inhibitor into seed crystals. Compounds haying a threshold effect particularly include polyphosphates haying a chain-like structure and include sequestering agent phosphonic acids, such as methylphosphonosuccinic acid or 2-phosphonobutane~l,2,4-tricarboxylic acid. However, condensed phosphates are not suitable for this purpose since they are split up by phosphatases in the body to give ineffective monophosphate. Moreover, tests have shown that, under the physiological conditions which prevail in the intestinal tract, the majority of sequestering agent phosphonic acids are either unsuitable or are not sufficiently effective.
It was therefore surprising that the above-cb/ h 3 _ ., , mentioned dicarboxydiphosphonic acids and their nontoxicpharmacologically acceptable water-soluble salts constitute suitable ingredients for the above preparation. The com-pounds are diphosphonoalkanedicarboxylic acids selected from the group consisting of l,l-diphosphonopropane-2,3-dlcarboxylic acid and 2,2-diphosphonobutane-3,4-dicarboxylic acid, with the former acid being preferred.
Instead of these acids, it is also possible to use their nontoxic pharmacologically acceptable, water-soluble salts, such as the alkali metal salts, for example, sodium and potassium, and the magnesium salts, and the ammonium and substituted ammonium salts such as the lower alkylol-ammonium salts, for example, the mono-, di- or tri- ethylolammonium salts. It is also possible to use the partial salts, in which only a proportion of the acidic protons is replaced by other cations. Partial salts, which produce a pH in the range ~om 6 to 8.5 in aqueous solution, are preferred. Mixtures of the above-mentioned acids and their salts can also be used.
The proportion of the precipitation inhibitors in the appetite curbing preparations containing an alginic com-pound is variable. However, this proportion must be great enough to inhibit the precipitation of calcium ions in the intestinal tract. This precipitation is possibly caused by the presence of calcium hardness (i.e., calcium ions) in the wate~. Based upon a 10 gm amount of the alginic compound, about 50 to 200 mg,preferably 100 to 200 mg, of the precipi-tation inhibitor can be present in compositions of the invention.
This corresp~nds to the weight ratio of l50 to 200):1 for the alginic compound to the precipitation inhibitor, equivalent to 1/2% to 2% of the inhibitor on the weight of the alginic compound. However, for the ressons as stated above, precipi-tation inhibitor is preferably present in substoichiometric cb/ ~ - 4 _ - lV~1013 amount based on the calcium required to gel said alginic compound.
Commercial alginic acid, or its nontoxic pharma-cologically acceptable water-soluble salts such as the alkali-metal salts, are suitable as the alginic ingredient. Potassium alginate or, preferably, sodium alginate can be used as alkali metal salts. Ammonium alginate can also be used. The pre-parations can be produced for administration in the form of tablets, pills or powder and may contain known ingredients such as sodium bicarbonate or Na2HPO4 as well as binding agents for the production of tablets. Further additives which may be present in the appetite curbing compositions are flavorings, vitamins and sugar/fruit concentrates.
Generally speaking, the appetite curbing composi-tions according to the invention contain from 25% to 50% by weight of the alginate-diphosphonic acid preparation, with the balance up to 100% by weight being the other known ingred-ients and/or additives mentioned aboye which constitute an inert nontoxic pharmacologically acceptable carrier.
The appetite curbing compositions are administered orally to warm-bloQded animals in units which contain an anoretically effective amount, or about 15 to 70 mg/kg of body weight ~preferably 25 to 50 mg/kg of body weight~, of the alginic-diphosphonic acid combination. These dosage units can be in the form of tablets, pills or powders and are con-veniently administered by dissolving the tablets, pills or powders of the combination in a suitable liquid medium such as water, milk, fruit juice or a carbonated beverage. The liquid medium contains from 0.5% to 5% by weight of the appetite ' 30 curbing composition, and can be consumed by drinking.
The appetite curbing preparations of the present invention have the advantage of preventing precipitation "
cb/ - 5 -:
or excessive sequestering of calcium ions. The ease of digest-ibility of the anoretic agent is greatly increased, even for sensitive persons.
The following examples illustrate the present invention without limiting it in any manner.
EXAMPLE
In order to test the activity of the compositions containing compounds which might be effective as precipitation inhibitors, the following experiments were carried out. 600 mg of sodium alginate was slowly stirred into 50 ml of a solution of sodium bicarbonate ~Na2HPO4) containing the inhibitor stated in Table I. After filling up to the final volume, the follow-ing concentrations were obtained per liter of alginate solution:
6 gm of sodium alginate 0.075 gm of precipitation inhibitor ; 2 gm of HC03 ions 0.1 gm of HPO4 ions The above concentrations of bicarbonate and hydrogen phosphate ions were approximately equivalent to the inorganic components of intestinal juice. The solution had a pH of 8.
As soon as the sodium alginate had homogeneously dissolved, - 50 ml of 40 dH ~German hardness) hard water was added, so that the sQlution had a calcium hardness of 20 dH. The : precipitatlon of calcium alginate became apparent through ~elling or clotting, whlch could readily be observed by means of deposlts on the walls of the container when the sample was shaken.
A control sample of the alginic compound was also mixed with the bicarbonate-hydrogen phosphate solution. The ; 30 results of the control test together with the results of the test with a composition of the inyention are reported in Table I. The results of the same tests with comparative ' ~h - cb/ - 6 -: ' ;: ' .:
', ' ' ~ ' ~ , ' ' ' 1~4~0~3 precipitation inhibitors are reported in Table II. The com-parative tests clearly indicate that the desired results are not achieved with other prior art compounds, even though these do in part have a yery similar sequestering effect.
Table I
ecipitation Inhibitor Results None ~control) Strong to very strong gelation l,l-Diphosphonopropane-
The present invention relates to appetite curbing compositions for mammals, methods for the preparation of such compositions, and methods for curbing the appetite of mammals by use of said compositions.
It is known to produce preparations based on alignates for use as appetite curbing agents in slimming diets. Since these preparations swell in the stomach and ~ `
intestinal tract, they produce a feeling of fullness and satisfaction in human beings. However, the preparations 10 have a considerable disadvantage in that in the presence of calcium ions they form calcium-containing deposits of low solubility. As a result, it is possible for a calcium ion deficiency to be produced, particularly in the intestinal tract. The fear has therefore often been voiced that dis-turbances of the metabolism could thereby be produced.
It is an object of the present invention to over-come the above-described drawbacks of the prior art.
It is another object of the present invention to proyide A preparation comprising alginic acid and a diphosphonic 20 acid ~or nontoxic pharmacologically acceptable water-soluble salts thereof~ in which the diphosphonic- acid acts as inhibitor of the precipitation of calcium salts; and thereby inhibits precipitation of calcium ions; this preparation is useful for curbing the appetite of a warm-blooded animal.
These and further objects of the present invention -~
will become apparent as the description thereof proceeds.
The present invention relates to alginic acid pre-parations containing a diphosphonic acid (or nontoxic pharma-cologically acceptable water-soluble salts thereof) as inhibitor 30 of the precipitation of calcium salts when the composition is ingested. This preparation is useful as an appetite curbing agent for warm-blooded animals.
cb/ - 1 -1(~410~3 Accordingly, the present invention provides a pre-paration for use in curbing the appetite of warm-blooded animals which comprises an alginic compound and a diphosphonic compound of the formula:
wherein Rl is hydrogen or methyl and the nontoxic pharma-cologically acceptable water-soluble salts thereof, as inhibitor of the precipitation of calcium salts when the composition is administered to warm-blooded animals.
More particularly, the present invention is directed to an appetite curbing preparation for warm-blooded animals comprising (A) an alginic compound selected from the groups consisting of alginic acid and the nontoxic pharmacologically acceptable water-soluble salts thereof, and ~ 3) a substoichiometric amount based on the calcium ions required to gel said ~lginic compound of a diphosphonic compound as precipitation inhibitor for calcium ions selected ; from the group consisting of a diphosphonic compound having the formula CH2 ~ IH ~ I R
wherein Rl is hydrogen or methyl and the nontoxic pharma-cologically acceptable water-soluble salts thereof.
Also, the present invention provides an appetite curbing composition for a warm-blooded animal consisting essen-tially of 25% to 50% by weight of the above appetite curbingpreparation and 50~ to 75% by weight of a nontoxic pharma-~ologically acceptable carrier.
,,,, ~
~- cb/ - 2 -In addition, the present invention provides a method for curbing the appetite of warm-blooded animals comprising ~ :
administering to said animals an anoretically effective amount of the appetite curbing preparation mentioned above.
Also, the present invention provides an improvement in a process for dieting, which consists essentially in con-suming ~during or before a meal) an effective amount of the appetite curbing preparation mentioned above as an anoretic material.
It has become apparent that in principle it is possible to preyent the formation of calcium alginate by add-ing thereto a strong sequestering agent, for example, nitrilo-triacetic acid or ethylenediaminetetraacetic acid. However, the calcium ions are thereby sequestered to such an extent that they may possibly no longer be available for physiological processes in the warm-blooded animal. Moreover, the precipi-tation of the calcium salts can be prevented for a consider-able period of time by using compounds which have a strong -~
inhibiting effect (threshold effect). In this case, crystalline growth is probably inhibited to a very great extent by the incorporation of the inhibitor into seed crystals. Compounds haying a threshold effect particularly include polyphosphates haying a chain-like structure and include sequestering agent phosphonic acids, such as methylphosphonosuccinic acid or 2-phosphonobutane~l,2,4-tricarboxylic acid. However, condensed phosphates are not suitable for this purpose since they are split up by phosphatases in the body to give ineffective monophosphate. Moreover, tests have shown that, under the physiological conditions which prevail in the intestinal tract, the majority of sequestering agent phosphonic acids are either unsuitable or are not sufficiently effective.
It was therefore surprising that the above-cb/ h 3 _ ., , mentioned dicarboxydiphosphonic acids and their nontoxicpharmacologically acceptable water-soluble salts constitute suitable ingredients for the above preparation. The com-pounds are diphosphonoalkanedicarboxylic acids selected from the group consisting of l,l-diphosphonopropane-2,3-dlcarboxylic acid and 2,2-diphosphonobutane-3,4-dicarboxylic acid, with the former acid being preferred.
Instead of these acids, it is also possible to use their nontoxic pharmacologically acceptable, water-soluble salts, such as the alkali metal salts, for example, sodium and potassium, and the magnesium salts, and the ammonium and substituted ammonium salts such as the lower alkylol-ammonium salts, for example, the mono-, di- or tri- ethylolammonium salts. It is also possible to use the partial salts, in which only a proportion of the acidic protons is replaced by other cations. Partial salts, which produce a pH in the range ~om 6 to 8.5 in aqueous solution, are preferred. Mixtures of the above-mentioned acids and their salts can also be used.
The proportion of the precipitation inhibitors in the appetite curbing preparations containing an alginic com-pound is variable. However, this proportion must be great enough to inhibit the precipitation of calcium ions in the intestinal tract. This precipitation is possibly caused by the presence of calcium hardness (i.e., calcium ions) in the wate~. Based upon a 10 gm amount of the alginic compound, about 50 to 200 mg,preferably 100 to 200 mg, of the precipi-tation inhibitor can be present in compositions of the invention.
This corresp~nds to the weight ratio of l50 to 200):1 for the alginic compound to the precipitation inhibitor, equivalent to 1/2% to 2% of the inhibitor on the weight of the alginic compound. However, for the ressons as stated above, precipi-tation inhibitor is preferably present in substoichiometric cb/ ~ - 4 _ - lV~1013 amount based on the calcium required to gel said alginic compound.
Commercial alginic acid, or its nontoxic pharma-cologically acceptable water-soluble salts such as the alkali-metal salts, are suitable as the alginic ingredient. Potassium alginate or, preferably, sodium alginate can be used as alkali metal salts. Ammonium alginate can also be used. The pre-parations can be produced for administration in the form of tablets, pills or powder and may contain known ingredients such as sodium bicarbonate or Na2HPO4 as well as binding agents for the production of tablets. Further additives which may be present in the appetite curbing compositions are flavorings, vitamins and sugar/fruit concentrates.
Generally speaking, the appetite curbing composi-tions according to the invention contain from 25% to 50% by weight of the alginate-diphosphonic acid preparation, with the balance up to 100% by weight being the other known ingred-ients and/or additives mentioned aboye which constitute an inert nontoxic pharmacologically acceptable carrier.
The appetite curbing compositions are administered orally to warm-bloQded animals in units which contain an anoretically effective amount, or about 15 to 70 mg/kg of body weight ~preferably 25 to 50 mg/kg of body weight~, of the alginic-diphosphonic acid combination. These dosage units can be in the form of tablets, pills or powders and are con-veniently administered by dissolving the tablets, pills or powders of the combination in a suitable liquid medium such as water, milk, fruit juice or a carbonated beverage. The liquid medium contains from 0.5% to 5% by weight of the appetite ' 30 curbing composition, and can be consumed by drinking.
The appetite curbing preparations of the present invention have the advantage of preventing precipitation "
cb/ - 5 -:
or excessive sequestering of calcium ions. The ease of digest-ibility of the anoretic agent is greatly increased, even for sensitive persons.
The following examples illustrate the present invention without limiting it in any manner.
EXAMPLE
In order to test the activity of the compositions containing compounds which might be effective as precipitation inhibitors, the following experiments were carried out. 600 mg of sodium alginate was slowly stirred into 50 ml of a solution of sodium bicarbonate ~Na2HPO4) containing the inhibitor stated in Table I. After filling up to the final volume, the follow-ing concentrations were obtained per liter of alginate solution:
6 gm of sodium alginate 0.075 gm of precipitation inhibitor ; 2 gm of HC03 ions 0.1 gm of HPO4 ions The above concentrations of bicarbonate and hydrogen phosphate ions were approximately equivalent to the inorganic components of intestinal juice. The solution had a pH of 8.
As soon as the sodium alginate had homogeneously dissolved, - 50 ml of 40 dH ~German hardness) hard water was added, so that the sQlution had a calcium hardness of 20 dH. The : precipitatlon of calcium alginate became apparent through ~elling or clotting, whlch could readily be observed by means of deposlts on the walls of the container when the sample was shaken.
A control sample of the alginic compound was also mixed with the bicarbonate-hydrogen phosphate solution. The ; 30 results of the control test together with the results of the test with a composition of the inyention are reported in Table I. The results of the same tests with comparative ' ~h - cb/ - 6 -: ' ;: ' .:
', ' ' ~ ' ~ , ' ' ' 1~4~0~3 precipitation inhibitors are reported in Table II. The com-parative tests clearly indicate that the desired results are not achieved with other prior art compounds, even though these do in part have a yery similar sequestering effect.
Table I
ecipitation Inhibitor Results None ~control) Strong to very strong gelation l,l-Diphosphonopropane-
2,3-dicarboxylic acid Weak gelation Table II
Precipitation Inhibitors tComparative) Results Methylenediphosphonic acid Strong to medium strong gelation Ethane-l,l-diphosphonic acid Strong to very strong gelation Propane-1,2,3-tri-phosphonic acid Strong gelation Methylphosphonosuccinic 20 acid yery strong gelation : 2-Phosphonobutane-1,2,4-tricarboxylic acid Medium strong gelation Amino-tris-(methylene- Strong to extremely strong phosphonic acid) gelation Dimethylaminomethane-diphosphonic acid Medium strong to strong gelation Aminoacetic acid-N,N-dimethylene-30 phosphonic acid Very strong gelation Chlorobenzyl-diphosphonic acid Strong to very strong gelation - Ethylenediamine-tetrakis-~methylene~
phosphonic acid) Strong to yery strong gelation Hexamethylenediamine-tetrakis-(methylene-phosphonic acid) Strong to very strong gelation Cyclohexanehexa-carboxylic acid Medium strong to strong gelation cb/ ~ - 7 -lV~10~3 A preparation which was suitable as an appetite curbing agent was prepared from the following composition by weight:
64.5% sugar/fruit concentrate 35% sodium alginate 0.5~ of the diphosphonic acid of Example 1 in the form of the sodium salt.
10 Approximately 6 gm of the anoretic preparation was placed in a dry glass and filled up with 200 gm of cold water while being stirred. The drink was imbibed approximately 15 minutes before the reduced meals.
Although the present inventlon has been disclosed in connection with a few preferred embodiments thereof, variations and modifications may be resorted to by those skilled in the art without departing from the principles of the new invention. All of these variations and modifications are considered to be within the true spirit and scope of the present invention as disclosed in the foregoing description and defined by the appen~ed claims.
':
..~.
,, ~/ - 8 -' , ~ , .
Precipitation Inhibitors tComparative) Results Methylenediphosphonic acid Strong to medium strong gelation Ethane-l,l-diphosphonic acid Strong to very strong gelation Propane-1,2,3-tri-phosphonic acid Strong gelation Methylphosphonosuccinic 20 acid yery strong gelation : 2-Phosphonobutane-1,2,4-tricarboxylic acid Medium strong gelation Amino-tris-(methylene- Strong to extremely strong phosphonic acid) gelation Dimethylaminomethane-diphosphonic acid Medium strong to strong gelation Aminoacetic acid-N,N-dimethylene-30 phosphonic acid Very strong gelation Chlorobenzyl-diphosphonic acid Strong to very strong gelation - Ethylenediamine-tetrakis-~methylene~
phosphonic acid) Strong to yery strong gelation Hexamethylenediamine-tetrakis-(methylene-phosphonic acid) Strong to very strong gelation Cyclohexanehexa-carboxylic acid Medium strong to strong gelation cb/ ~ - 7 -lV~10~3 A preparation which was suitable as an appetite curbing agent was prepared from the following composition by weight:
64.5% sugar/fruit concentrate 35% sodium alginate 0.5~ of the diphosphonic acid of Example 1 in the form of the sodium salt.
10 Approximately 6 gm of the anoretic preparation was placed in a dry glass and filled up with 200 gm of cold water while being stirred. The drink was imbibed approximately 15 minutes before the reduced meals.
Although the present inventlon has been disclosed in connection with a few preferred embodiments thereof, variations and modifications may be resorted to by those skilled in the art without departing from the principles of the new invention. All of these variations and modifications are considered to be within the true spirit and scope of the present invention as disclosed in the foregoing description and defined by the appen~ed claims.
':
..~.
,, ~/ - 8 -' , ~ , .
Claims (10)
OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An appetite curbing composition for warm-blooded animals comprising (A) an alginic compound selected from the groups consisting of alginic acid and the nontoxic pharmacologically acceptable water-soluble salts thereof, and (B) a substoichiometric amount based on the calcium required to gel said alginic compound of a diphosphonic compound having the formula:
wherein R1 is selected from the group consisting of hydrogen and methyl;and the nontoxic pharmacologically acceptable water-soluble salts thereof.
wherein R1 is selected from the group consisting of hydrogen and methyl;and the nontoxic pharmacologically acceptable water-soluble salts thereof.
2. The appetite curbing composition of Claim 1 wherein the weight of said diphosphonic compound is 0.5% to 2% of the weight of said alginic compound.
3. A composition according to Claim 1 wherein R1 is hydrogen.
4, A composition according to Claim 1 wherein R1 is methyl.
5. A composition according to Claim 1 wherein the diphosphonic compound is a 1,1-diphosphonopropane-2.3-dicarboxylic acid salt.
6. A composition according to Claim 1 in which said alginic and diphosphonic compounds are present as partial salts which produce a pH in the range of 6 to 8.5 when dissolved in water.
7. A composition according to Claim 1 wherein said salts are selected from the group consisting of the alkali metal, magnesium, ammonium and loweralkanol ammonium salts, and mixtures thereof.
8. An appetite curbing composition for a warm-blooded animal consisting essentially of from 25% to 50% by weight of the appetite curbing composition of Claim 1, and from 50% to 75% by weight of a nontoxic pharmacologically accept-able carrier therefor.
9. A composition according to Claim 1 in unit dose pill form.
10. An aqueous solution containing 0.5% to 5% by weight of the composition of Claim 8.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2412827A DE2412827A1 (en) | 1974-03-16 | 1974-03-16 | ALGINATE PREPARATIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041013A true CA1041013A (en) | 1978-10-24 |
Family
ID=5910341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,248A Expired CA1041013A (en) | 1974-03-16 | 1975-03-04 | Appetite curbing preparation containing an alginate and a diphosphonic acid |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT347037B (en) |
| BE (1) | BE826675A (en) |
| CA (1) | CA1041013A (en) |
| DE (1) | DE2412827A1 (en) |
| DK (1) | DK61775A (en) |
| FR (1) | FR2263704B1 (en) |
| GB (1) | GB1480967A (en) |
| NL (1) | NL7501972A (en) |
| SE (1) | SE404289B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2065046B1 (en) | 2007-11-30 | 2013-07-31 | Kao Corporation | Gip secretion inhibitor |
| US8338389B2 (en) | 2009-06-17 | 2012-12-25 | Kao Corporation | Agent for preventing or ameliorating obesity |
-
1974
- 1974-03-16 DE DE2412827A patent/DE2412827A1/en active Pending
-
1975
- 1975-02-19 SE SE7501886A patent/SE404289B/en unknown
- 1975-02-19 NL NL7501972A patent/NL7501972A/en unknown
- 1975-02-19 DK DK61775*#A patent/DK61775A/da unknown
- 1975-03-04 CA CA221,248A patent/CA1041013A/en not_active Expired
- 1975-03-12 GB GB10225/75A patent/GB1480967A/en not_active Expired
- 1975-03-14 BE BE154319A patent/BE826675A/en unknown
- 1975-03-14 FR FR7507977A patent/FR2263704B1/fr not_active Expired
- 1975-03-14 AT AT197375A patent/AT347037B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2263704B1 (en) | 1978-12-08 |
| SE404289B (en) | 1978-10-02 |
| DK61775A (en) | 1975-09-17 |
| GB1480967A (en) | 1977-07-27 |
| DE2412827A1 (en) | 1975-09-25 |
| SE7501886L (en) | 1975-09-17 |
| AT347037B (en) | 1978-12-11 |
| NL7501972A (en) | 1975-09-18 |
| ATA197375A (en) | 1978-04-15 |
| FR2263704A1 (en) | 1975-10-10 |
| BE826675A (en) | 1975-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0034034B1 (en) | Nutrient composition | |
| US5215750A (en) | L-glutamine and vitamin-containing compositions effective for inducing weight loss and for weight control | |
| US3505082A (en) | Salt substitute composition | |
| US3924017A (en) | Sweetness inducer | |
| AU666654B2 (en) | Calcium, trace mineral, vitamin D and drug therapy combinations | |
| Rastogi et al. | Selenium and lead: mutual detoxifying effects | |
| WO1992005711A1 (en) | Tooth enamel erosion inhibitor | |
| US4125608A (en) | Appetite curbing preparation containing an alginate and a diphosphonic acid | |
| US4839172A (en) | Composition of accelerating recovery of function of hematopoietic organs | |
| CA1041013A (en) | Appetite curbing preparation containing an alginate and a diphosphonic acid | |
| WO2002096449A1 (en) | Carbohydrate modifying agent and drinks containing the modifying agent | |
| AU2002305703A1 (en) | Carbohydrate modifying agent and drinks containing the modifying agent | |
| Thomas et al. | Some concepts concerning the genesis of urinary calculi | |
| RU2002130196A (en) | PHARMACEUTICAL COMPOSITION CONTAINING CALCIUM OR CALCIUM AND VITAMIN MIXTURE OR CALCIUM AND MAGNESIUM MIXTURE | |
| Christensen et al. | Effects of divalent amino acids on iron absorption | |
| US20040048925A1 (en) | Composition and method for enhancing the bioavailability of calcium and magnesium in dietary supplements and food additives | |
| JPS58165774A (en) | Drink composition | |
| US20040220266A1 (en) | Composition and method for enhancing the bioavailability of calcium and magnesium in dietary supplements and food additives | |
| Freeman et al. | Acute effects of acetazolamide (Diamox) on plasma and urinary electrolytes of dogs with special reference to calcium | |
| US5348749A (en) | Method for treating panic disorder | |
| US4681756A (en) | Prevention of N-nitroso compound formation in vivo | |
| Apgar | Use of EDTA to produce zinc deficiency in the pregnant rat | |
| JPH02119761A (en) | Calcium lactate-containing drink and solid preparation | |
| EP0377119A1 (en) | Agent for reducing adverse effects of table salt | |
| Lutzeyer et al. | Drug therapy of urinary calculi and prevention of recurrence |