JPS5933563B2 - アスピリン／茶共沈物の製造法 - Google Patents
アスピリン／茶共沈物の製造法Info
- Publication number
- JPS5933563B2 JPS5933563B2 JP48119475A JP11947573A JPS5933563B2 JP S5933563 B2 JPS5933563 B2 JP S5933563B2 JP 48119475 A JP48119475 A JP 48119475A JP 11947573 A JP11947573 A JP 11947573A JP S5933563 B2 JPS5933563 B2 JP S5933563B2
- Authority
- JP
- Japan
- Prior art keywords
- tea
- solution
- aspirin
- coprecipitate
- added
- 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
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims description 103
- 229960001138 acetylsalicylic acid Drugs 0.000 title claims description 101
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 241001122767 Theaceae Species 0.000 title claims 2
- 239000000243 solution Substances 0.000 claims description 100
- 235000013616 tea Nutrition 0.000 claims description 95
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- 229960000583 acetic acid Drugs 0.000 claims description 41
- 239000012362 glacial acetic acid Substances 0.000 claims description 39
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 38
- 238000003756 stirring Methods 0.000 claims description 32
- 235000020344 instant tea Nutrition 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 239000004471 Glycine Substances 0.000 claims description 19
- 239000007853 buffer solution Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 244000269722 Thea sinensis Species 0.000 description 98
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 60
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 30
- 229960004889 salicylic acid Drugs 0.000 description 30
- 239000012153 distilled water Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- JZLOKWGVGHYBKD-UHFFFAOYSA-M sodium;2-acetyloxybenzoate Chemical compound [Na+].CC(=O)OC1=CC=CC=C1C([O-])=O JZLOKWGVGHYBKD-UHFFFAOYSA-M 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- 229920001864 tannin Polymers 0.000 description 17
- 235000018553 tannin Nutrition 0.000 description 17
- 239000001648 tannin Substances 0.000 description 17
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 239000006071 cream Substances 0.000 description 13
- 238000010908 decantation Methods 0.000 description 11
- 230000003110 anti-inflammatory effect Effects 0.000 description 10
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 10
- 239000002518 antifoaming agent Substances 0.000 description 9
- 230000000740 bleeding effect Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 208000032843 Hemorrhage Diseases 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 235000006468 Thea sinensis Nutrition 0.000 description 8
- 238000000975 co-precipitation Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 229960001948 caffeine Drugs 0.000 description 5
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 239000012086 standard solution Substances 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 206010053155 Epigastric discomfort Diseases 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000007605 air drying Methods 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 241000209507 Camellia Species 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000018597 common camellia Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 3
- 235000011957 flavonols Nutrition 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 210000001156 gastric mucosa Anatomy 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 235000008118 thearubigins Nutrition 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 239000001263 FEMA 3042 Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 235000020279 black tea Nutrition 0.000 description 2
- 208000034158 bleeding Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229940067596 butylparaben Drugs 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 229940071162 caseinate Drugs 0.000 description 2
- 229920002770 condensed tannin Polymers 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
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- 239000010419 fine particle Substances 0.000 description 2
- 150000007946 flavonol Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- -1 glacial acetic acid Chemical class 0.000 description 2
- 239000003978 infusion fluid Substances 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 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
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- 238000005554 pickling Methods 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000014620 theaflavin Nutrition 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004457 water analysis Methods 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/82—Theaceae (Tea family), e.g. camellia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/148—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with compounds of unknown constitution, e.g. material from plants or animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Botany (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Rheumatology (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pain & Pain Management (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Alternative & Traditional Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Tea And Coffee (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30079672A | 1972-10-25 | 1972-10-25 | |
| US40494573A | 1973-10-10 | 1973-10-10 | |
| US404945 | 1982-08-04 | ||
| US300796 | 1994-09-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4993519A JPS4993519A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-05 |
| JPS5933563B2 true JPS5933563B2 (ja) | 1984-08-16 |
Family
ID=26971986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48119475A Expired JPS5933563B2 (ja) | 1972-10-25 | 1973-10-25 | アスピリン／茶共沈物の製造法 |
Country Status (18)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54122259A (en) * | 1978-03-13 | 1979-09-21 | Kyowa Hakko Kogyo Co Ltd | Aluminum acetylsalicylate glutaminate |
| DE3603576A1 (de) * | 1986-02-06 | 1987-08-13 | Code Kaffee Handel | Verwendung von gerbstoffen und/oder chlorogensaeure sowie nahrungs-, genuss- und/oder arzneimittel mit gerbstoff- und/oder chlorogensaeurezusatz |
| DE102006004912A1 (de) | 2006-01-20 | 2007-07-26 | Rheinmetall Waffe Munition Gmbh | System zum Schutz insbesondere großer fliegender Plattformen vor infrarot- bzw. radargelenkter Bedrohungen |
| EP2432485B1 (en) | 2009-05-19 | 2013-07-31 | Unilever PLC | Prebiotic composition |
| DE102014200045A1 (de) * | 2014-01-07 | 2015-07-09 | Ralph Nussbaum | Polyphenol-Konjugate |
| JP6367623B2 (ja) * | 2014-07-04 | 2018-08-01 | 美紀 坂巻 | 水棲原虫駆除剤およびその製造方法 |
-
1970
- 1970-10-29 IL IL43512A patent/IL43512A0/xx unknown
-
1973
- 1973-10-15 CA CA183,398A patent/CA1018459A/en not_active Expired
- 1973-10-18 IE IE1867/73A patent/IE40139B1/xx unknown
- 1973-10-20 IN IN2335/CAL/73A patent/IN139752B/en unknown
- 1973-10-23 NO NO734097A patent/NO140748C/no unknown
- 1973-10-23 NL NLAANVRAGE7314546,A patent/NL176142C/xx not_active IP Right Cessation
- 1973-10-23 DE DE2353087A patent/DE2353087C2/de not_active Expired
- 1973-10-23 PH PH15143A patent/PH12248A/en unknown
- 1973-10-23 FR FR7337765A patent/FR2204415B1/fr not_active Expired
- 1973-10-23 GB GB4938773A patent/GB1391747A/en not_active Expired
- 1973-10-23 SE SE7314372A patent/SE423487B/xx unknown
- 1973-10-23 BE BE136957A patent/BE806392A/xx not_active IP Right Cessation
- 1973-10-24 ES ES419913A patent/ES419913A1/es not_active Expired
- 1973-10-24 FI FI733303A patent/FI51428C/fi active
- 1973-10-24 CH CH1498073A patent/CH604721A5/xx not_active IP Right Cessation
- 1973-10-24 AR AR250676A patent/AR199592A1/es active
- 1973-10-24 DK DK576473AA patent/DK134096B/da unknown
- 1973-10-25 JP JP48119475A patent/JPS5933563B2/ja not_active Expired
- 1973-10-29 IL IL43512A patent/IL43512A/en unknown
Also Published As
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