WO1997017976A1 - Microcellulose-based preparations - Google Patents
Microcellulose-based preparations Download PDFInfo
- Publication number
- WO1997017976A1 WO1997017976A1 PCT/EP1996/004961 EP9604961W WO9717976A1 WO 1997017976 A1 WO1997017976 A1 WO 1997017976A1 EP 9604961 W EP9604961 W EP 9604961W WO 9717976 A1 WO9717976 A1 WO 9717976A1
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- WO
- WIPO (PCT)
- Prior art keywords
- microcellulose
- fibres
- preparations
- intestinal
- effect
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 14
- 230000001105 regulatory effect Effects 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 7
- 239000002775 capsule Substances 0.000 claims abstract description 6
- 230000037406 food intake Effects 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 230000000968 intestinal effect Effects 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 16
- 235000005911 diet Nutrition 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 230000008991 intestinal motility Effects 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 230000037213 diet Effects 0.000 claims description 5
- 230000001965 increasing effect Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 230000000378 dietary effect Effects 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 208000007502 anemia Diseases 0.000 claims description 2
- 230000007794 irritation Effects 0.000 claims description 2
- 230000035935 pregnancy Effects 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 abstract description 11
- 239000001913 cellulose Substances 0.000 abstract description 11
- 235000010980 cellulose Nutrition 0.000 abstract description 10
- 229920000168 Microcrystalline cellulose Polymers 0.000 abstract description 9
- 239000008108 microcrystalline cellulose Substances 0.000 abstract description 9
- 235000019813 microcrystalline cellulose Nutrition 0.000 abstract description 9
- 229940016286 microcrystalline cellulose Drugs 0.000 abstract description 9
- 230000002496 gastric effect Effects 0.000 abstract description 2
- 235000013311 vegetables Nutrition 0.000 description 9
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 8
- 229920000609 methyl cellulose Polymers 0.000 description 8
- 239000001923 methylcellulose Substances 0.000 description 8
- 235000010981 methylcellulose Nutrition 0.000 description 8
- 229960002900 methylcellulose Drugs 0.000 description 8
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- 206010010774 Constipation Diseases 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
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- 150000007513 acids Chemical class 0.000 description 5
- 230000009471 action Effects 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
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- 229940105329 carboxymethylcellulose Drugs 0.000 description 4
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- 239000003814 drug Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 210000001072 colon Anatomy 0.000 description 3
- 235000013325 dietary fiber Nutrition 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
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- 239000008141 laxative Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920000715 Mucilage Polymers 0.000 description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 230000030136 gastric emptying Effects 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229940125722 laxative agent Drugs 0.000 description 2
- 230000002475 laxative effect Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000002949 phytic acid Nutrition 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010000060 Abdominal distension Diseases 0.000 description 1
- 241001116389 Aloe Species 0.000 description 1
- 102100026189 Beta-galactosidase Human genes 0.000 description 1
- 239000010369 Cascara Substances 0.000 description 1
- 235000006693 Cassia laevigata Nutrition 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000556215 Frangula purshiana Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 108010059881 Lactase Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 244000134552 Plantago ovata Species 0.000 description 1
- 235000003421 Plantago ovata Nutrition 0.000 description 1
- 108010001267 Protein Subunits Proteins 0.000 description 1
- 239000009223 Psyllium Substances 0.000 description 1
- 241000219093 Rhamnus Species 0.000 description 1
- 241000735631 Senna pendula Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 208000019790 abdominal distention Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical class O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008953 bacterial degradation Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 208000024330 bloating Diseases 0.000 description 1
- 229940058505 cascara Drugs 0.000 description 1
- 239000000799 cathartic agent Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 229960001577 dantron Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 229940116108 lactase Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000008291 lyophilic colloid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940070687 psyllium Drugs 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229940124513 senna glycoside Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A61K31/716—Glucans
- A61K31/717—Celluloses
-
- 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
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
Definitions
- dietary fibres the main indigestible alimentary constituent
- dietary fibres have found a wide application in the treatment of constipation.
- the term dietary fibres is referred to the total natural fibrosic contents available in aliments, mainly of vegetable origin, which cannot be chemically digested by the enzymatic system of humans.
- classification of dietary fibres is referred to the residues of indigestible vegetables and can be summarized as follows:
- Cellulose is a polysaccharide (C 6 H ⁇ o0 5 ) whose molecular weight ranges from 300.000 to 500.000, formed by linear chains of D- glucose molecules linked together by beta bonds.
- Alimentary fibres consist of millions of cellulose molecules linked together in chains, whose length may even reach several tens of centimeters or meters. Beta bonds are undigested by mammals " enzymatic systems (for instance, starch has alpha bonds).
- Cellulose is the main structural constituent of vegetable cell walls. It is insoluble in distilled water and acids.
- Non-cellulosic fibres consist of non-cellulosic polysaccharides comprising emicelluloses, pectines, mucillages and other media derived by algae, resins and lignin. Besides water absorption, non-cellulosic fibres have also other collateral effects due to their chelant action as they seem to be able to chelate biliary salts and cholesterol, thus reducing their abso ⁇ tion; however, this effect is unfortunately reached also with drugs and minerals, such as iron, calcium and zinc. Further, resins and soluble fibres contained therein may undergo a bacterial digestion in the colon, and elicit short-chain volatile fat acids and gas production (carbon dioxide and methane).
- Methyl-cellulose and carboxymethyl-cellulose derived from it are products obtained by synthesis, which modify the chemical- physical characteristics of cellulose, i.e. from insoluble to soluble in cold water and insoluble in hot water.
- Solubility is a function of the number of methylic units used as substituents; the products known on the market have a 1,8 substitution degree, i.e. they contain about 29% methossilic units.
- Methyl-cellulose and carboxymethyl-cellulose can be converted into gel.
- microcellulose to be vehiculated in pharmaceutical forms suitable for ingestion tablettes, granular or powder form, etc.
- ingestion tablettes, granular or powder form, etc.
- preparations suitable to cover either partially or totally the requirements of alimentary fibres in humans or animals or in preparations to regulate intestinal transit, preferably suitable for the use in all conditions of altered intestinal motility due to an insufficient or viceversa excessive water retention, first in the alimentary bolus and then in stools, where microcellulose affects in a regulatory manner the solid-fluid ratio during intestinal transit.
- Microcrystalline cellulose or microcellulose is a preparation of fragments of cellulose crystallite units in the form of a non fibrosic powder, containing particles in the form of rigid small bars, whose refraction index is 1.55.
- the molecular weight of the basic component, microcellulose can range as required from 10.000 to 300.000, i.e. between a range of numbers of atoms classified from 10 4 to IO 9 , whose dimensions allow a liophile colloidal dispersion.
- Availability of different molecular weights of microcrystalline cellulose allow to graduate the number of molecule in any given unit of weight, thus to improve or reduce the osmolar effect ofthe product. Examples of how microcrystalline cellulose is synthesised are described in US Patents nos. 2,978,476 and US 3,141,875.
- Microcrystalline cellulose or microcellulose is featured by its peculiar property of being slightly soluble in diluted alcaline solutions, whereas it is totally insoluble in acids and does not gelify under any conditions.
- microcellulose is fully inactive in the stomach and just a light solubility can be foreseen in the continuation of the gastrointestinal transit with pH raise. Moreover, unlike methyl- cellulose, microcrystalline cellulose will not dissolve in any water volume.
- microcellulose to obtain a regulatory effect on intestinal motility due to its chemical-physical characteristics. This has the pu ⁇ ose of obviating to the problems caused by alimentary fibres available so far on the market, such as subordination to water volume, digestion of part of their constituents and often unendurable production of large intestinal gas volumes, their chelating effect con pharmaceutical products and some minerals salts.
- microcellulose is provided for use under those conditions where alimentary fibres are not tolerated, being excessively irritant and eliciting a too fast, frequent and irritant intestinal transit of bolus volume. Microcellulose is not digested by mammals because they have no cellulase, i.e. the enzyme required to break beta bonds between D- glucose molecules. For this reason, microcellulose will not cause, as of itself, any problems related to the digestion of sugars contained in the fibres or alimentary fibres. 7
- microcellulose Due to the relatively small molecular size in respect to cellulosic fibres (containing milions of closely interlaced cellulose units for total macroscopic sizes), microcellulose is also featured by a lower water eagerness and unlike water soluble methyl-cellulose it is insoluble in water.
- microcellulose will yield a number of molecules as liophile dispersion to the water available with or contained in the aliments, as a fixed proportion of the water- microcellulose ratio (as it can be easily proved by gradually adding water volumes to a fixed cellulose volume: a progressive reduction of the precipitate will in fact show up with increasing volumes of solvents; however, it will remain a precipitate also with a 1000:1 water-cellulose weight ratio).
- a gradual "bulking" effect will be obtained, which is easily dosable for progressive dose increases.
- microcellulose will develop through its insolubility an efficient absorbing effect in all those conditions where an excessive intestinal transit speed is caused by intestinal inability to reabsorb water.
- This condition occurs and has a clinical significance eg. in the case of irritable colon syndrome, characterized by alternating alvus, i.e. repeated alternation of constipation and stools.
- Such a condition is often related to the intestine intolerance to some sugars available in the aliments that cannot be digested at all, or to an oversensitivity to vegetable long fibers, or both of them.
- the intestinal bacterial flora will rapidly convert lactose into lactic acid, carbon dioxide and water, stressing both the irritant effect and transit speed, and alternating strong abdominal distention and pains. While the therapy will obviously require a reduction or removal of milk products, introduction of microcellulose according to the present invention has a regulatory effect on the bolus and makes it consistent, however it will not lead to the overdistention phenomena as caused by fibres of vegetable origin, right for the limited swelling capacity of microcellulose.
- microcellulose does not contain any constituents capable of a further incentive for bacterial degradation with gas production.
- Microcrystalline cellulose is a polyhydroxyaldheide, thus it has a slight polarity between the terminal portion which is lyophilic and the initial portion which is hydrophilic. In our experiments this characteristic of the molecule allows either an important and irreversible dispersion of oil in water media, or a reduction in capillary water pressures. Thus, reducing the size of oil drops in food introduced by diet and water adhesiveness, the introduction of sufficient amounts of microcrystalline cellulose would improve also gastric emptying. This phenomenon has never been described before. On the contrary, all alimentary fibers are well known and clinically used for the pu ⁇ ose to slow gastric emptying, bloating being the subjective consequence which very frequently leeds to discontinuation of fibers introduction.
- microcellulose vehiculated in pharmaceutical forms for ingestion (tablets, capsules or granular and/or powder form) is indicated as the main or sole active constituent in preparations for use in all conditions of altered intestinal motility due to insufficient or viceversa excessive water presence, first in the alimentary bolus and then in stools. Due to its insoluble characteristics (unlike soluble methyl-cellulose and carboxymethyl-cellulose) that make it an ideal lyophilic colloid, microcellulose develops a regulatory effect on the solid-fluid ratio during intestinal transit. It is apparent how according to the present invention microcellulose is indicated for use as the main or sole active ingredient in preparations adequately covering either partially or totally the requirements of undigested fibres in the alimentary diet of humans and animals.
- microcellulose in this frame can be used as an ideal dietetic integrator in all pathologic conditions where fibres assumption is contraindicated since irritation is caused by an excessive length of fibres.
- microcellulose according to the present invention is indicated as an ideal dietetic integrator in all conditions where the intestinal assumption of fibres should be maintained or increased, but this is contraindicated because of the risk of malabso ⁇ tion induced by them on calcium and iron (eg. osteoporosis, pregnancy, sideropoor anaemia, etc.).
- microcellulose is an ideal integrator of undigested fibres for its dimensional, chemical-physical and organolectic characteristics, having an ideal regulatory effect in all conditions of decreased intestinal motility and above all in all conditions where other undigested fibrous residues are not tolerated and even contraindicated for therapeutic pu ⁇ oses.
- microcellulose can also be used as a constituent for association with other molecules, to modulate the preponderant effect of some substances (eg. a strong hydrophilous effect of methyl-cellulose and psyllium) or stress the reducing tensio-active effect of other substances (eg. symeticone).
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
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Abstract
According to the invention, a dimensionally specific physical form of polycellobiose, also called microcrystalline cellulose or microcellulose, is vehiculated in pharmaceutical forms suitable for ingestion (such as capsules, tablets, granula or powder forms, etc.) in order to obtain a regulatory effect on gastro-intestinal transit, in all conditions where cellulose and other fibres may not be well tolerated or are contraindicated.
Description
MICROCELLULOSE-BASED PREPARATIONS
Description
All kind of therapeutic approaches to treatment of constipation have important biases peculiarly on long term treatment schedules. Diphenylmethane (phenolphtalein, pysacodil) and antraquinone containing laxatives of vegetable origin (cascara, senna, rhamnus, danthron, aloe) have been targeted as suitable only for very short period or extemporary treatment of constipation for their potential risks by government health, food and drug agencies of different countries. On the other hand, saline cathartics (magnesium, sodium phosphate and potassium salt) cannot be used chronically and are potentially dangerous because of calcium and water excessive losses, and can thus inducing malabsorption of soluble drugs and vitamins. Their use is limited also by pain as frequent collateral effect. In the last two decades, mainly as a result of epidemiologic studies on large populations, the role of fibres, the main indigestible alimentary constituent, has been focused by nutritionists. This is mainly due to their role in the possible prevention of colon carcinoma as well as to their regulatory effect on dimensions, consistence and speed of intestinal transit. For this reason, dietary fibres have found a wide application in the treatment of constipation. The term dietary fibres is referred to the total natural fibrosic contents available in aliments, mainly of vegetable origin, which cannot be chemically digested by the enzymatic system of humans.
One of the nutritional problem lies in the fact that, on average, occidental diets lack a sufficient amount of fibres, due to the treatments that food undergoes during its preparatory stages (as an example, bran is removed from wheat grains when transformed in flour). According to the U.S. National Health and Nutrition
Examination Survey, the average daily fibre introduction in U.S.A. is 1 1 g/die, whereas a reasonable recommendation calls for 20-25 g/die.
Entering more into details, classification of dietary fibres is referred to the residues of indigestible vegetables and can be summarized as follows:
1. cellulose; 2. non-cellulosic fibres.
1. Cellulose
Cellulose is a polysaccharide (C6Hιo05) whose molecular weight ranges from 300.000 to 500.000, formed by linear chains of D- glucose molecules linked together by beta bonds.
Alimentary fibres consist of millions of cellulose molecules linked together in chains, whose length may even reach several tens of centimeters or meters. Beta bonds are undigested by mammals" enzymatic systems (for instance, starch has alpha bonds).
Cellulose is the main structural constituent of vegetable cell walls. It is insoluble in distilled water and acids.
2. Non-cellulosic fibres Non-cellulosic fibres consist of non-cellulosic polysaccharides comprising emicelluloses, pectines, mucillages and other media derived by algae, resins and lignin. Besides water absorption, non-cellulosic fibres have also other
collateral effects due to their chelant action as they seem to be able to chelate biliary salts and cholesterol, thus reducing their absoφtion; however, this effect is unfortunately reached also with drugs and minerals, such as iron, calcium and zinc. Further, resins and soluble fibres contained therein may undergo a bacterial digestion in the colon, and elicit short-chain volatile fat acids and gas production (carbon dioxide and methane). The use of mixed alimentary fibres, either cellulosic or not, has become common use in the treatment of constipation, in the form of "bulk forming" laxatives, due to their water retention capability. The size of fibres seems to have a determining action as the longer the fibres are the bulkier will they become with fluid. As a matter of fact, the previous technique uses fibre mixtures of alimentary origin whose chain is the longest possible to maximize the "bulk forming" effect, with all the relevant implications on water retention inside and its chelating effect on various biologic molecules (specifically biliary salts and fat acids). Moreover, the phytate contents of vegetable fibres is significant during calcium and iron based treatments, where phytates have a chelating action that reduces their bioavailability substantially.
The use of methyl-cellulose is known for laxative purposes due to its specific water absoφtion and solubility properties. Methyl-cellulose and carboxymethyl-cellulose derived from it are products obtained by synthesis, which modify the chemical- physical characteristics of cellulose, i.e. from insoluble to soluble in cold water and insoluble in hot water.
Solubility is a function of the number of methylic units used as substituents; the products known on the market have a 1,8
substitution degree, i.e. they contain about 29% methossilic units. Methyl-cellulose and carboxymethyl-cellulose can be converted into gel.
Therefore, the pharmacologic laxative effect according to the known state of art can be summarized as follows:
- increase of alimentary bolus and stools,
- increase of water contents, with accelerated ileum transit,
- increased quantity in the colon of biliary salts available in the stools due to the chelating effect, - eliciting gas production and increased presence of free fat acids due to bacterial digestion of aliments escaped to digestion as they were bulk entrapped and/or of constituents of said alimentary fibres entrapped by the bacterial intestinal flora.
It is the object of the present invention to overcome the problems of the previous technique. In particular, the aim of the research leading to the identification of the present invention was to solve the limit and problems posed by actual knowledge and state of the art, by corresponding to all the following requirements:
- physical not chemical action; - emulsionant action on water-oily interfacies;
- easily controlled, dose-related osmolarity;
- bulk forming, dose related effect;
- no caloric contribution;
- indigestibility by human digestive enzymes - no chemical interaction with drugs.
These characteristics would be appropriate for an ideal regulator of intestinal motility, suitable for acute or chronic safe use. According to the present invention this object is obtained with the
use of microcellulose to be vehiculated in pharmaceutical forms suitable for ingestion (tablets, capsules, granular or powder form, etc.) as the sole or main active ingredient in preparations suitable to cover either partially or totally the requirements of alimentary fibres in humans or animals, or in preparations to regulate intestinal transit, preferably suitable for the use in all conditions of altered intestinal motility due to an insufficient or viceversa excessive water retention, first in the alimentary bolus and then in stools, where microcellulose affects in a regulatory manner the solid-fluid ratio during intestinal transit.
Further objects and advantages of the present invention will be apparent from the following detailed description, which is supplied by way of an explanatory but non limiting example. Microcrystalline cellulose or microcellulose is a preparation of fragments of cellulose crystallite units in the form of a non fibrosic powder, containing particles in the form of rigid small bars, whose refraction index is 1.55.
The molecular weight of the basic component, microcellulose, can range as required from 10.000 to 300.000, i.e. between a range of numbers of atoms classified from 104 to IO9, whose dimensions allow a liophile colloidal dispersion. Availability of different molecular weights of microcrystalline cellulose allow to graduate the number of molecule in any given unit of weight, thus to improve or reduce the osmolar effect ofthe product. Examples of how microcrystalline cellulose is synthesised are described in US Patents nos. 2,978,476 and US 3,141,875. Microcrystalline cellulose or microcellulose is featured by its peculiar property of being slightly soluble in diluted alcaline
solutions, whereas it is totally insoluble in acids and does not gelify under any conditions.
Therefore, microcellulose is fully inactive in the stomach and just a light solubility can be foreseen in the continuation of the gastrointestinal transit with pH raise. Moreover, unlike methyl- cellulose, microcrystalline cellulose will not dissolve in any water volume.
Chemical-physical characteristics of microcrystalline cellulose to form a sol have provided a new indication for its use as emulsifier, foam-repellent and thickening agent.
However, it is the object of the present invention to use microcellulose to obtain a regulatory effect on intestinal motility due to its chemical-physical characteristics. This has the puφose of obviating to the problems caused by alimentary fibres available so far on the market, such as subordination to water volume, digestion of part of their constituents and often unendurable production of large intestinal gas volumes, their chelating effect con pharmaceutical products and some minerals salts. In addition, according to the present invention, microcellulose is provided for use under those conditions where alimentary fibres are not tolerated, being excessively irritant and eliciting a too fast, frequent and irritant intestinal transit of bolus volume. Microcellulose is not digested by mammals because they have no cellulase, i.e. the enzyme required to break beta bonds between D- glucose molecules. For this reason, microcellulose will not cause, as of itself, any problems related to the digestion of sugars contained in the fibres or alimentary fibres.
7
Due to the relatively small molecular size in respect to cellulosic fibres (containing milions of closely interlaced cellulose units for total macroscopic sizes), microcellulose is also featured by a lower water eagerness and unlike water soluble methyl-cellulose it is insoluble in water.
Therefore, a given quantity of microcellulose will yield a number of molecules as liophile dispersion to the water available with or contained in the aliments, as a fixed proportion of the water- microcellulose ratio (as it can be easily proved by gradually adding water volumes to a fixed cellulose volume: a progressive reduction of the precipitate will in fact show up with increasing volumes of solvents; however, it will remain a precipitate also with a 1000:1 water-cellulose weight ratio). Thus, a gradual "bulking" effect will be obtained, which is easily dosable for progressive dose increases.
Further, microcellulose will develop through its insolubility an efficient absorbing effect in all those conditions where an excessive intestinal transit speed is caused by intestinal inability to reabsorb water. This condition occurs and has a clinical significance eg. in the case of irritable colon syndrome, characterized by alternating alvus, i.e. repeated alternation of constipation and stools. Such a condition is often related to the intestine intolerance to some sugars available in the aliments that cannot be digested at all, or to an oversensitivity to vegetable long fibers, or both of them.
The patient suffers from constipation if fibres are eliminated, whereas he will suffers from diarrhea when vegetables and/or milk products are introduced. Colon irritability, in fact, is often due to a
lack of intestinal lactase (i.e. the enzyme capable of separating the lactose unit in two sub-units, namely galactose and glucose). The resulting overosmolarity of the alimentary bolus would anyway lead to an intestinal bolus containing an excessive water volume, all the more if long vegetable fibres are contained therein, which have an enormous swelling capacity.
Moreover, when the bolus reaches the intestine, the intestinal bacterial flora will rapidly convert lactose into lactic acid, carbon dioxide and water, stressing both the irritant effect and transit speed, and alternating strong abdominal distention and pains. While the therapy will obviously require a reduction or removal of milk products, introduction of microcellulose according to the present invention has a regulatory effect on the bolus and makes it consistent, however it will not lead to the overdistention phenomena as caused by fibres of vegetable origin, right for the limited swelling capacity of microcellulose.
Moreover, the reduced length of the particles forming it will not lead to any overdistention phenomena due to formation of large boluses difficult to fraction and having a reduced absoφtion surface; moreover, since the precipitate-dispersion ratio of microcellulose is a function of water volume, there will be a self- regulation between the dispersed and non-dispersed part percentage, suitable to maintain the best possible solid-fluid ratio, i.e. providing a regulatory action. On the contrary, methyl -cellulose and carboxymethyl-cellulose, which are strongly soluble in water, only tend to maintain the water volume present in the intestinal lumen at a maximum level, operating solely as transit or stool bolus accelerators.
Unlike alimentary fibres (bran, mucillages, etc.), microcellulose does not contain any constituents capable of a further incentive for bacterial degradation with gas production.
Microcrystalline cellulose is a polyhydroxyaldheide, thus it has a slight polarity between the terminal portion which is lyophilic and the initial portion which is hydrophilic. In our experiments this characteristic of the molecule allows either an important and irreversible dispersion of oil in water media, or a reduction in capillary water pressures. Thus, reducing the size of oil drops in food introduced by diet and water adhesiveness, the introduction of sufficient amounts of microcrystalline cellulose would improve also gastric emptying. This phenomenon has never been described before. On the contrary, all alimentary fibers are well known and clinically used for the puφose to slow gastric emptying, bloating being the subjective consequence which very frequently leeds to discontinuation of fibers introduction.
Therefore, according to the present invention, microcellulose vehiculated in pharmaceutical forms for ingestion (tablets, capsules or granular and/or powder form) is indicated as the main or sole active constituent in preparations for use in all conditions of altered intestinal motility due to insufficient or viceversa excessive water presence, first in the alimentary bolus and then in stools. Due to its insoluble characteristics (unlike soluble methyl-cellulose and carboxymethyl-cellulose) that make it an ideal lyophilic colloid, microcellulose develops a regulatory effect on the solid-fluid ratio during intestinal transit. It is apparent how according to the present invention microcellulose
is indicated for use as the main or sole active ingredient in preparations adequately covering either partially or totally the requirements of undigested fibres in the alimentary diet of humans and animals. Therefore, in this frame microcellulose can be used as an ideal dietetic integrator in all pathologic conditions where fibres assumption is contraindicated since irritation is caused by an excessive length of fibres. Likewise, microcellulose according to the present invention is indicated as an ideal dietetic integrator in all conditions where the intestinal assumption of fibres should be maintained or increased, but this is contraindicated because of the risk of malabsoφtion induced by them on calcium and iron (eg. osteoporosis, pregnancy, sideropoor anaemia, etc.). According to the above description the characteristics of the present invention will be apparent, as it is obvious also for its advantages. Specifically, as described above it will be apparent how microcellulose is an ideal integrator of undigested fibres for its dimensional, chemical-physical and organolectic characteristics, having an ideal regulatory effect in all conditions of decreased intestinal motility and above all in all conditions where other undigested fibrous residues are not tolerated and even contraindicated for therapeutic puφoses. Finally, microcellulose can also be used as a constituent for association with other molecules, to modulate the preponderant effect of some substances (eg. a strong hydrophilous effect of methyl-cellulose and psyllium) or stress the reducing tensio-active effect of other substances (eg. symeticone).
Claims
1. The use of microcellulose, to be vehiculated in pharmaceutical forms suitable for ingestion (tablets, capsules, granular and powder form, etc.) as the sole or main active ingredient in preparations suitable to cover either partially or totally the requirements of undigested fibres in the diet of humans or animals.
2. The use of microcellulose according to Claim 1 in preparations suitable to act as a dietetic integrator in all pathologic conditions, where fibres assumption is contraindicated due to irritation caused by an excessive fibre size.
3. The use of microcellulose according to Claim 1 in preparations suitable to act as a dietetic integrator in all pathologic conditions, where the intestinal assumption of fibres should be maintained or increased, but is contraindicated because of the risk of malabsoφtion induced by them on calcium and iron (eg. osteoporosis, pregnancy, sideropoor anaemia, etc.).
4. The use of microcellulose according to Claim 1 in preparations having a regulatory effect on the solid-fluid ratio during intestinal transit, in all pathologic conditions of altered intestinal motility due to insufficient or viceversa excessive water presence first in the alimentary bolus and then in stools.
5. The use of microcellulose according to one or more of the above Claims, for association with other molecules to modulate their preponderant effect or stress the reducing tensio-active effect of other substances.
6. Preparations having a regulatory effect on intestinal transit, in particular suitable for use in all conditions of altered intestinal motility due to insufficient or viceversa excessive water presence, first in the alimentary bolus and then in stools, characterized in that they comprise microcellulose in pharmaceutical form suitable for ingestion (tablets, capsules, granular and powder form), as the sole or main active ingredient having a regulatory effect on the solid- fluid ratio during intestinal transit.
7. Preparations suitable to cover either partially or totally the requirements of undigested fibres in the diet of humans or animals, characterized in that they comprise microcellulose in pharmaceutical forms suitable for ingestion (tablets, capsules, granular and powder form) as the sole or main active ingredient.
8. Preparations comprising microcellulose according to the above description and for the puφoses as specified.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU76232/96A AU7623296A (en) | 1995-11-14 | 1996-11-13 | Microcellulose-based preparations |
| EP96939020A EP0861083A1 (en) | 1995-11-14 | 1996-11-13 | Microcellulose-based preparations |
| JP9518574A JP2000502048A (en) | 1995-11-14 | 1996-11-13 | Microcellulose preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITTO95A000917 | 1995-11-14 | ||
| IT95TO000917A IT1290792B1 (en) | 1995-11-14 | 1995-11-14 | MICROCELLULOSE BASED PREPARATIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997017976A1 true WO1997017976A1 (en) | 1997-05-22 |
Family
ID=11413961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1996/004961 WO1997017976A1 (en) | 1995-11-14 | 1996-11-13 | Microcellulose-based preparations |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0861083A1 (en) |
| JP (1) | JP2000502048A (en) |
| AR (1) | AR008987A1 (en) |
| AU (1) | AU7623296A (en) |
| IT (1) | IT1290792B1 (en) |
| WO (1) | WO1997017976A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8993551B2 (en) | 2002-10-16 | 2015-03-31 | Alan Ferguson | Composition for the regulation of the human immune system and the prevention and treatment of diseases thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023104A (en) * | 1960-07-05 | 1962-02-27 | American Viscose Corp | Food compositions incorporating cellulose crystallite aggregates |
| EP0317079A2 (en) * | 1987-11-19 | 1989-05-24 | Orlando A. Battista | High-fiber, expandable, dry-mixed compositions |
| JPH01319421A (en) * | 1988-06-17 | 1989-12-25 | Hajime Inamoto | Molded product for improving constipation, promoting bowel movement, and improving stool quality for people lacking dietary fiber |
| US5342636A (en) * | 1992-05-05 | 1994-08-30 | Bakshi Amarjit S | Process for modifying a fibrous bulking agent |
-
1995
- 1995-11-14 IT IT95TO000917A patent/IT1290792B1/en active IP Right Grant
-
1996
- 1996-11-13 AU AU76232/96A patent/AU7623296A/en not_active Abandoned
- 1996-11-13 JP JP9518574A patent/JP2000502048A/en active Pending
- 1996-11-13 WO PCT/EP1996/004961 patent/WO1997017976A1/en not_active Application Discontinuation
- 1996-11-13 EP EP96939020A patent/EP0861083A1/en not_active Withdrawn
- 1996-11-14 AR ARP960105185A patent/AR008987A1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023104A (en) * | 1960-07-05 | 1962-02-27 | American Viscose Corp | Food compositions incorporating cellulose crystallite aggregates |
| EP0317079A2 (en) * | 1987-11-19 | 1989-05-24 | Orlando A. Battista | High-fiber, expandable, dry-mixed compositions |
| JPH01319421A (en) * | 1988-06-17 | 1989-12-25 | Hajime Inamoto | Molded product for improving constipation, promoting bowel movement, and improving stool quality for people lacking dietary fiber |
| US5342636A (en) * | 1992-05-05 | 1994-08-30 | Bakshi Amarjit S | Process for modifying a fibrous bulking agent |
Non-Patent Citations (1)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN vol. 014, no. 118 (C - 0697) 6 March 1990 (1990-03-06) * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8993551B2 (en) | 2002-10-16 | 2015-03-31 | Alan Ferguson | Composition for the regulation of the human immune system and the prevention and treatment of diseases thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000502048A (en) | 2000-02-22 |
| AR008987A1 (en) | 2000-03-08 |
| AU7623296A (en) | 1997-06-05 |
| ITTO950917A1 (en) | 1997-05-14 |
| EP0861083A1 (en) | 1998-09-02 |
| IT1290792B1 (en) | 1998-12-10 |
| ITTO950917A0 (en) | 1995-11-14 |
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