EP0258339A1 - Verwendung von gerbstoffen und/oder chlorogensäure sowie nahrungs-, genu und/oder arzneimittel mit gerbstoff- und/oder chlorogensäurezusatz - Google Patents
Verwendung von gerbstoffen und/oder chlorogensäure sowie nahrungs-, genu und/oder arzneimittel mit gerbstoff- und/oder chlorogensäurezusatzInfo
- Publication number
- EP0258339A1 EP0258339A1 EP87901423A EP87901423A EP0258339A1 EP 0258339 A1 EP0258339 A1 EP 0258339A1 EP 87901423 A EP87901423 A EP 87901423A EP 87901423 A EP87901423 A EP 87901423A EP 0258339 A1 EP0258339 A1 EP 0258339A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- gastric
- tannins
- chlorogenic acid
- acid
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920001864 tannin Polymers 0.000 title claims abstract description 37
- 235000018553 tannin Nutrition 0.000 title claims abstract description 37
- 239000001648 tannin Substances 0.000 title claims abstract description 37
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 title claims abstract description 36
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 title claims abstract description 34
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 title claims abstract description 34
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 title claims abstract description 34
- 229940074393 chlorogenic acid Drugs 0.000 title claims abstract description 34
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 title claims abstract description 34
- 235000001368 chlorogenic acid Nutrition 0.000 title claims abstract description 34
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 title claims abstract description 34
- 239000003814 drug Substances 0.000 title claims abstract description 17
- 229940079593 drug Drugs 0.000 title claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 title claims description 17
- 239000000021 stimulant Substances 0.000 title abstract description 6
- -1 foodstuffs Substances 0.000 title 1
- 210000001156 gastric mucosa Anatomy 0.000 claims abstract description 20
- 235000013305 food Nutrition 0.000 claims abstract description 13
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000005487 catechin Nutrition 0.000 claims abstract description 6
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims abstract description 5
- 229950001002 cianidanol Drugs 0.000 claims abstract description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 12
- 230000002496 gastric effect Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 7
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 230000028327 secretion Effects 0.000 abstract description 5
- 210000004211 gastric acid Anatomy 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 7
- 210000004051 gastric juice Anatomy 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 208000032843 Hemorrhage Diseases 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 206010061164 Gastric mucosal lesion Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010017788 Gastric haemorrhage Diseases 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 208000034158 bleeding Diseases 0.000 description 2
- 150000001765 catechin Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000002183 duodenal effect Effects 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- NRHBUMVXUGSZAT-IVUGMLEJSA-N (3R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical class O[C@@H]1CC(O)(C[C@@](O)(C1O)C(=O)\C=C\c1ccc(O)c(O)c1)C(O)=O NRHBUMVXUGSZAT-IVUGMLEJSA-N 0.000 description 1
- YCTSCXLOPJCPDH-UHFFFAOYSA-N 2-(3,7-dimethyl-2,6-dioxopurin-1-yl)acetic acid Chemical class CN1C(=O)N(CC(O)=O)C(=O)C2=C1N=CN2C YCTSCXLOPJCPDH-UHFFFAOYSA-N 0.000 description 1
- 125000005273 2-acetoxybenzoic acid group Chemical group 0.000 description 1
- CWVRJTMFETXNAD-GMZLATJGSA-N 5-Caffeoyl quinic acid Natural products O[C@H]1C[C@](O)(C[C@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-GMZLATJGSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000196324 Embryophyta 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
- 102220547770 Inducible T-cell costimulator_A23L_mutation Human genes 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 229940030225 antihemorrhagics Drugs 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008845 cholagoga Substances 0.000 description 1
- 229940124571 cholagogue Drugs 0.000 description 1
- 239000000731 choleretic agent Substances 0.000 description 1
- 230000001989 choleretic effect Effects 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000002874 hemostatic agent Substances 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000008673 vomiting Effects 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/10—Treating roasted coffee; Preparations produced thereby
- A23F5/14—Treating roasted coffee; Preparations produced thereby using additives, e.g. milk or sugar; Coating
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
Definitions
- Tannin or catechin-based tannin agents and / or isolated chlorogenic acid or their physiologically compatible deriv tives have the effect, when used before or during the absorption of foodstuffs, stimulants and / or medicines which activ the secretion of gastric acid and / or irritate or attack the gastric mucous membrane, of reducing the secretion of gastric ac and / or of protecting the gastric mucous membrane.
- Tannins based on tannin or catechin and / or isolated chlorogenic acid or their physiologically tolerable derivatives lead, when used, before or at the same time as the administration of food, food and / or / which stimulates gastric acid secretion and / or irritates or attacks the gastric mucosa. or medicines to reduce gastric acid secretion and / or to protect the gastric mucosa.
- tannins and / or chlorogenic acid as well as food, luxury foods and / or medicinal products with added tannins and / or chlorogenic acid
- duodenal ulcer, ventricular ulcer and other gastric mucosal lesions which are often stress and / or medication-induced, can bleed or perforate in a life-threatening manner.
- Non-steroidal anti-inflammatory drugs NSAIDs
- NSAIDs Non-steroidal anti-inflammatory drugs
- acetylsalicylic acid can lead to gastric bleeding; the same applies to the other NSAIDs, e.g. Indomethacin (see R. Bruhn et al., Progress in Medicine 100 (36), 1661 to 168 (1982)).
- Therapy with acetylsalicylic acid and other drugs from the NSAID group carries a defined risk, so that before using these drugs, their therapeutic benefits must be weighed against the accompanying risk.
- the invention is therefore based on the object of finding a means by which the gastric mucosa can be protected against the development of ulcerations in such a way that food, luxury foods and / or medications that damage the gastric mucosa can be administered without disturbing side effects up to life-threatening bleeding and perforations.
- tannins based on tannins or catechins or agents based on isolated chlorogenic acid or their physiologically tolerable derivatives are suitable for protecting the gastric mucosa against food, luxury foods and / or drugs who are known to damage the gastric and duodenal mucosa or to stimulate gastric acid secretion.
- the tannins or the chlorogenic acid are applied before or simultaneously with the administration of the agents mentioned.
- chlorogenic acid means the mono- and dicaffeoylquinic acids and mixtures thereof.
- the 3-, 4- and 5-caffeoylquinic acids or their mixture, in particular the 3-caffeoylquinic acid, are particularly preferred.
- the acids can be used as free acid or in the form of their physiologically compatible derivatives, in particular salts or esters.
- the alkali salts, especially the potassium salts, are particularly suitable.
- the derivatives mentioned can be used instead of the free acid, since the acid is released from them in the strongly acidic gastric environment.
- Chlorogenic acid is a compound found in numerous plants, for example in green coffee beans, which was isolated by Freudenberg in 1920, the structure of which has been elucidated, and which was later also synthesized (see Merck Index, 10th edition, No. 2112). From a publication by V. Istudor et al., Farmacia 29, 41 to 48 (1981) it is known that a from Calendulae
- Flores available extract can be used as stomach tea for the treatment of gastric and duodenal ulcers. It is reported that the extract includes Contains alantoin, caffeinic acid and polyphenol derivatives, including chlorogenic acid. Chlorogenic acid is said to be a choleretic and cholagogue. A synergism between the different components of the examined extract is suspected.
- chlorogenic acid as a pure substance has a protective effect on the gastric mucosa. This is apparently due to the fact that under the action of chlorogenic acid a superficial protective film is formed which protects the gastric mucosa. At the same time, the stimulated gastric acid secretion decreases. These effects may be due to an astringent or tanning effect of chlorogenic acid, similar to that of tanning agents.
- the hydrolyzable ester-like tannins and / or their derivatives are particularly preferred as tanning agents.
- These tannins are esters of sugars, especially glucose, with various hydroxybenzoic acids, especially 3, 4, 5-trihydroxybenzoic acid (gallic acid).
- the non-ester-like, condensed tannins which are primarily compounds from the group of catechins, such as those found in tea, can also be used.
- the various tannins are commercially available; as a rule, these are mixtures of compounds which are obtained from natural raw materials.
- the tannins are known to have an astringent and hemostatic effect. They are used externally as hemostatic agents and for the treatment of local burns (sunburn). It is also known to use tannins Treatment of diarrhea, ie to use catarrhal diseases of the intestinal tract. For this purpose, tannins for complexes with protein (tannin albumin) are used in order to ensure that the tannin is only released in the intestine, that is, it is not yet effective in the stomach.
- tannins for complexes with protein tannins for complexes with protein (tannin albumin) are used in order to ensure that the tannin is only released in the intestine, that is, it is not yet effective in the stomach.
- tannins or chlorogenic acid are able to protect the gastric or duodenal mucosa from aggressive foodstuffs, foods and medicines which stimulate acid secretion.
- the agents according to the invention form a whitish, net-like coating immediately after contact with the mucous membrane, which acts like a protective film.
- 10% alcohol is applied as an irritant, there is no change in the area protected in this way, while the untreated gastric mucosa shows pathological reddening.
- the tannins or the chlorogenic acid are preferably prepared in such a way that they are released only in the stomach. This can be done in a manner known per se by using a coating in the manufacture of tablets which only dissolves in the acidic gastric environment.
- the agents can be administered either before or preferably at the same time as the agents against which the gastric mucosa is to be protected. As far as it concerns foodstuffs or stimulants, it concerns those which contain practically no tannins or chlorogenic acid or an insufficient amount thereof, but which are converted into a more stomach-friendly form by the addition according to the invention can be.
- the invention is of particular importance in connection with active pharmaceutical ingredients which damage the gastric mucosa in such a way that ulcers or bleeding can occur.
- a particular problem in this regard is acetylsalicylic acid and the other NSAIDs, which many patients take regularly as an analgesic or anti-rheumatic and can then lead to the side effects described in the gastrointestinal tract.
- acetylsalicylic acid or the other NSAID with tannins and / or chlorogenic acid in a dosage form that releases the active substances in the gastric juice, the gastric mucosa can be effectively protected, with the result that gastric mucosal lesions or bleeding are no longer observed.
- the combination preparations according to the invention are preferably administered to fasting patients in order to prevent the added tannins from being rendered ineffective by reaction with proteins from the diet.
- a particularly favorable dosage form e.g. in the form of a core / shell tablet with the active substance as the core and the protective substances (tannins and / or chlorogenic acid) in the outer shell
- first the tannin or chlorogenic acid and then the active substance are released.
- the test subjects received 250 ml of coffee samples 1 to 5.
- the gastric juice extracted at time 0 was returned.
- 5 ml gastric juice were siphoned off.
- the gastric juice was then quantitatively removed at intervals of 15 minutes.
- the titratable acid determined with 0.1N NaOH, in Table 2 the values found are given in ml NaOH.
- the volume of gastric juice extracted is given in Table 2 in ml.
- the period t 60-150 was used for the comparative evaluation of the results, since it is known that the first 60 minutes after eating are overlaid by various other effects.
- Coffee samples Nos. 1 to 5 had an identical degree of roasting, but contained increasing amounts of chlorogenic acid. As the results shown in Table 2 show, coffee 1 leads to the highest acid stimulation, with increasing chlorogenic acid content the gastric acid secretion decreases significantly. Volume secretion also decreases in the order of coffee types 1 to 5. The influence of chlorogenic acid on the reduction of human gastric acid secretion stimulated by coffee roasting agents is obvious.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Non-Alcoholic Beverages (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863603576 DE3603576A1 (de) | 1986-02-06 | 1986-02-06 | Verwendung von gerbstoffen und/oder chlorogensaeure sowie nahrungs-, genuss- und/oder arzneimittel mit gerbstoff- und/oder chlorogensaeurezusatz |
| DE3603576 | 1986-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0258339A1 true EP0258339A1 (de) | 1988-03-09 |
Family
ID=6293456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87901423A Withdrawn EP0258339A1 (de) | 1986-02-06 | 1987-02-03 | Verwendung von gerbstoffen und/oder chlorogensäure sowie nahrungs-, genu und/oder arzneimittel mit gerbstoff- und/oder chlorogensäurezusatz |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4865847A (da) |
| EP (1) | EP0258339A1 (da) |
| JP (1) | JPS63502349A (da) |
| DE (1) | DE3603576A1 (da) |
| DK (1) | DK524087A (da) |
| FI (1) | FI874361A7 (da) |
| WO (1) | WO1987004619A1 (da) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3760463D1 (en) * | 1986-02-06 | 1989-09-28 | Code Kaffee Handel | Coffee and process for its production |
| AU7876491A (en) * | 1990-05-03 | 1991-11-27 | G.D. Searle & Co. | Pharmaceutical composition |
| US5629013A (en) * | 1991-04-04 | 1997-05-13 | The Procter & Gamble Company | Chewable calcium carbonate antacid tablet compositions |
| FR2693105B1 (fr) * | 1992-07-01 | 1994-09-02 | Oreal | Composition cosmétique et/ou dermatologique à action dépigmentante contenant un acide di- ou tri-caféoylquinique ou un mélange de ceux-ci. |
| TW255880B (da) * | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| US6696485B1 (en) | 1996-04-02 | 2004-02-24 | Mars, Incorporated | Procyanidin and cyclo-oxygenase modulator compositions |
| JP4350910B2 (ja) * | 1999-04-13 | 2009-10-28 | サイジェニック カンパニー リミテッド | ハイドロキシシンナム酸誘導体又はこれを含むトウキ抽出物を含有する痴呆予防及び治療用の組成物 |
| RU2286778C2 (ru) * | 2000-03-22 | 2006-11-10 | Марс, Инк. | Применение процианидинов какао в сочетании с ацетилсалициловой кислотой как противотромбоцитного терапевтического средства |
| WO2002076456A1 (en) * | 2001-03-27 | 2002-10-03 | Nutricia, N.V. | Method for inhibiting apoptosis of stem cells |
| US8206741B2 (en) | 2001-06-01 | 2012-06-26 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
| JP2006160721A (ja) * | 2004-11-09 | 2006-06-22 | Kao Corp | 大脳疲労回復剤 |
| EA201100313A1 (ru) | 2008-09-09 | 2011-10-31 | Астразенека Аб | Способ доставки фармацевтической композиции пациенту, нуждающемуся в этом |
| CA2764963C (en) | 2009-06-25 | 2016-11-01 | Astrazeneca Ab | Method for treating a patient at risk for developing an nsaid-associated ulcer |
| EP2340808A1 (en) * | 2009-12-21 | 2011-07-06 | I.R.B. Istituto Di Ricerche Biotecnologiche S.r.l. | Synergic combination of phenylpropanoids, such as verbascoside or teupolioside, and mesalamine |
| BR112014016085A8 (pt) | 2011-12-28 | 2017-07-04 | Pozen Inc | composições aprimoradas e métodos para distribuição de omeprazol mais ácido acetilsalicílico |
| EP2756765B1 (de) * | 2013-01-17 | 2019-03-27 | Symrise AG | Pharmazeutische Zubereitungen |
| CN103360435B (zh) * | 2013-06-09 | 2016-09-07 | 陕西师范大学 | 一种响应面法优化山茱萸果核中鞣质的提取工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES407523A1 (es) * | 1971-10-13 | 1975-11-16 | Robins Co Inc A H | Un procedimiento para la preparar un coprecitado de un agenteantiinflamatorio y acido tanico. |
| US4003999A (en) * | 1972-10-25 | 1977-01-18 | A. H. Robins Company, Incorporated | Aspirin-tea coprecipitates for treating inflammation |
| IL43512A0 (en) * | 1972-10-25 | 1974-03-14 | Robins Co Inc A H | Aspirin-tea coprecipitates and their preparation |
| GB1509979A (en) * | 1975-11-28 | 1978-05-10 | Fisons Ltd | Pharmaceutical compositions containing aspirin or indomethacin |
| DE2657896C3 (de) * | 1976-12-21 | 1979-12-06 | Dobrivoje Dr. 8000 Muenchen Tomic | Mittel mit blutstillender und entzündungshemmender Wirkung |
| JPS60192555A (ja) * | 1984-03-13 | 1985-10-01 | Osaka Chem Lab | 抗アレルギ−食品 |
| JPS60243016A (ja) * | 1984-05-17 | 1985-12-03 | Tsumura Juntendo Inc | 抗インフルエンザウイルス剤 |
-
1986
- 1986-02-06 DE DE19863603576 patent/DE3603576A1/de not_active Withdrawn
-
1987
- 1987-02-03 US US07/123,854 patent/US4865847A/en not_active Expired - Lifetime
- 1987-02-03 WO PCT/EP1987/000052 patent/WO1987004619A1/de not_active Ceased
- 1987-02-03 EP EP87901423A patent/EP0258339A1/de not_active Withdrawn
- 1987-02-03 FI FI874361A patent/FI874361A7/fi not_active IP Right Cessation
- 1987-02-03 JP JP62501519A patent/JPS63502349A/ja active Pending
- 1987-10-06 DK DK524087A patent/DK524087A/da not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8704619A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI874361A0 (fi) | 1987-10-05 |
| JPS63502349A (ja) | 1988-09-08 |
| DK524087D0 (da) | 1987-10-06 |
| FI874361L (fi) | 1987-10-05 |
| US4865847A (en) | 1989-09-12 |
| FI874361A7 (fi) | 1987-10-05 |
| DE3603576A1 (de) | 1987-08-13 |
| DK524087A (da) | 1987-10-06 |
| WO1987004619A1 (fr) | 1987-08-13 |
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Inventor name: GOESSWEIN, CLAUS, F. |