JPS5923313B2 - （＋）カテキンの水溶性複塩およびその製造方法 - Google Patents
（＋）カテキンの水溶性複塩およびその製造方法Info
- Publication number
- JPS5923313B2 JPS5923313B2 JP55119632A JP11963280A JPS5923313B2 JP S5923313 B2 JPS5923313 B2 JP S5923313B2 JP 55119632 A JP55119632 A JP 55119632A JP 11963280 A JP11963280 A JP 11963280A JP S5923313 B2 JPS5923313 B2 JP S5923313B2
- Authority
- JP
- Japan
- Prior art keywords
- catechin
- acid
- water
- salt
- basic amino
- 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
- 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 title claims description 40
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 title claims description 34
- 235000005487 catechin Nutrition 0.000 title claims description 34
- 229950001002 cianidanol Drugs 0.000 title claims description 29
- 150000003839 salts Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000243 solution Substances 0.000 claims description 19
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 235000001014 amino acid Nutrition 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000004472 Lysine Substances 0.000 claims description 8
- 235000019766 L-Lysine Nutrition 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 235000010323 ascorbic acid Nutrition 0.000 claims description 6
- 239000011668 ascorbic acid Substances 0.000 claims description 6
- 229960005070 ascorbic acid Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 3
- 229930064664 L-arginine Natural products 0.000 claims description 3
- 235000014852 L-arginine Nutrition 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 3
- 229930013915 (+)-catechin Natural products 0.000 claims 10
- 235000007219 (+)-catechin Nutrition 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
- 150000001765 catechin Chemical class 0.000 description 7
- 229960003646 lysine Drugs 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 210000002808 connective tissue Anatomy 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229940097043 glucuronic acid Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KWTQSFXGGICVPE-UHFFFAOYSA-N 2-amino-5-(diaminomethylideneamino)pentanoic acid;hydron;chloride Chemical compound Cl.OC(=O)C(N)CCCN=C(N)N KWTQSFXGGICVPE-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000081822 Uncaria gambir Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- -1 amino acid salt Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 210000001188 articular cartilage Anatomy 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 208000015100 cartilage disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 201000005043 chondromalacia Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229940025708 injectable product Drugs 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicinal Preparation (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/071,076 US4285964A (en) | 1979-08-30 | 1979-08-30 | Salts of (+)-catechine, their preparation and use, and compositions containing these salts |
| US71076 | 2002-02-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5655386A JPS5655386A (en) | 1981-05-15 |
| JPS5923313B2 true JPS5923313B2 (ja) | 1984-06-01 |
Family
ID=22099096
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55119632A Expired JPS5923313B2 (ja) | 1979-08-30 | 1980-08-29 | （＋）カテキンの水溶性複塩およびその製造方法 |
| JP59007386A Expired JPS5946947B2 (ja) | 1979-08-30 | 1984-01-20 | （＋）カテキン塩 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59007386A Expired JPS5946947B2 (ja) | 1979-08-30 | 1984-01-20 | （＋）カテキン塩 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4285964A (enExample) |
| JP (2) | JPS5923313B2 (enExample) |
| AT (1) | AT372381B (enExample) |
| BE (1) | BE884743A (enExample) |
| CA (1) | CA1172259A (enExample) |
| CH (1) | CH646412A5 (enExample) |
| DE (1) | DE3031710C2 (enExample) |
| DK (1) | DK153948C (enExample) |
| ES (1) | ES8106513A1 (enExample) |
| FI (1) | FI72724C (enExample) |
| FR (1) | FR2464262A1 (enExample) |
| GB (1) | GB2057437B (enExample) |
| GR (1) | GR69849B (enExample) |
| IE (1) | IE50231B1 (enExample) |
| IT (1) | IT1193979B (enExample) |
| NL (1) | NL183080C (enExample) |
| NO (1) | NO156010C (enExample) |
| SE (1) | SE448455B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507314A (en) * | 1983-07-20 | 1985-03-26 | Midit, Societe Fiduciaire | Drug for treating affections provoked by a too high histamine level, of the gastroduodenal mucosa and allergic affections |
| EP0263132A4 (en) * | 1986-04-07 | 1988-11-16 | Clemetson Ab Charles | ASCORBIC ACID COATED WITH CATECHIN AND METHOD. |
| US4857320A (en) * | 1987-02-19 | 1989-08-15 | Monsanto Company | Method of enhancing the solubility of tissue plasminogen activator |
| JPH0662408B2 (ja) * | 1987-10-01 | 1994-08-17 | 太陽化学株式会社 | 抗う蝕及び抗歯周病組成物 |
| JPH0672091B2 (ja) * | 1988-04-13 | 1994-09-14 | 太陽化学株式会社 | 抗う蝕組成物 |
| US5090785A (en) * | 1990-07-31 | 1992-02-25 | Stamp John R | Multi-compartment container |
| CA2143515A1 (en) * | 1994-03-22 | 1995-09-23 | Prakash Parab | Method for enhancing the rate of skin permeation of lactic acid through use of the l-enantiomer |
| GB2306321A (en) * | 1995-10-24 | 1997-05-07 | Anne Child | The use of (+)-catechin in the treatment or prophylaxis of connective tissue disorders |
| GB9700912D0 (en) | 1997-01-17 | 1997-03-05 | Chiroscience Ltd | Resolution |
| US5804594A (en) * | 1997-01-22 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for improving wrinkles and other skin conditions |
| WO2001013865A1 (en) | 1999-08-20 | 2001-03-01 | Howard Murad | Pharmaceutical compositions and methods for reducing the appearance of cellulite |
| US20030224071A1 (en) * | 1999-08-20 | 2003-12-04 | Howard Murad | Pharmaceutical compositions and methods for managing connective tissue ailments |
| US7252834B2 (en) | 2005-04-25 | 2007-08-07 | Clemson University Research Foundation (Curf) | Elastin stabilization of connective tissue |
| US20100069476A1 (en) * | 2005-05-17 | 2010-03-18 | Mitsui Norin Co., Ltd | Compositions and methods for reduction of cutaneous photoageing |
| WO2011014563A1 (en) | 2009-07-29 | 2011-02-03 | Vatrix Medical, Inc. | Tissue stabilization for heart failure |
| WO2011104667A1 (en) * | 2010-02-25 | 2011-09-01 | Anthem Biosciences Private Limited | Basic aminoacid salts of polyphenols |
| US8911468B2 (en) | 2011-01-31 | 2014-12-16 | Vatrix Medical, Inc. | Devices, therapeutic compositions and corresponding percutaneous treatment methods for aortic dissection |
| JP2014516695A (ja) | 2011-05-18 | 2014-07-17 | バトリックス・メディカル・インコーポレイテッド | 血管安定化用被覆バルーン |
| BE1023772B9 (fr) | 2013-05-17 | 2017-08-02 | Valore | Composition a base d'un complexe de (+)-catechine et d'acide amine pour le traitement et la prevention du cancer |
| BE1022579A9 (fr) * | 2014-11-10 | 2016-10-06 | Valore | Composition antimétastatique comprenant au moins un composé de type flavanol |
| TWI761672B (zh) | 2018-04-23 | 2022-04-21 | 日商阿爾卑斯藥品工業股份有限公司 | O-醣苷基類黃酮之組成物 |
| US10617705B1 (en) | 2019-01-24 | 2020-04-14 | Alps Pharmaceutical Ind. Co., Ltd. | Isoquercitrin compositions |
| US10918654B1 (en) | 2019-09-23 | 2021-02-16 | Alps Pharmaceutical Ind. Co., Ltd. | Rutin compositions |
| US11110109B2 (en) | 2019-10-22 | 2021-09-07 | Alps Pharmaceutical Ind. Co., Ltd. | Water soluble O-glycosyl flavonoid compositions and methods for preparing same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3270003A (en) * | 1964-08-07 | 1966-08-30 | Rayonier Inc | Iron complexed sulfonated polyflavonoids and their preparation |
| FR2128207B1 (enExample) * | 1971-03-11 | 1974-08-02 | Zyma Sa | |
| GB1575004A (en) * | 1976-03-23 | 1980-09-17 | Iverni Della Beffa Spa | Pharmacologically active polyphenolic substances |
| US4255336A (en) * | 1977-11-25 | 1981-03-10 | Ciba-Geigy Corporation | Process for the preparation of O-substituted derivatives of (+)-cyanidan-3-01 |
-
1979
- 1979-08-30 US US06/071,076 patent/US4285964A/en not_active Expired - Lifetime
-
1980
- 1980-08-12 BE BE0/201729A patent/BE884743A/fr not_active IP Right Cessation
- 1980-08-19 GB GB8026982A patent/GB2057437B/en not_active Expired
- 1980-08-20 GR GR62700A patent/GR69849B/el unknown
- 1980-08-21 DK DK358980A patent/DK153948C/da not_active IP Right Cessation
- 1980-08-22 DE DE3031710A patent/DE3031710C2/de not_active Expired
- 1980-08-22 SE SE8005890A patent/SE448455B/sv not_active IP Right Cessation
- 1980-08-22 FI FI802652A patent/FI72724C/fi not_active IP Right Cessation
- 1980-08-26 AT AT0432080A patent/AT372381B/de active
- 1980-08-27 IT IT24310/80A patent/IT1193979B/it active
- 1980-08-27 CH CH645780A patent/CH646412A5/fr not_active IP Right Cessation
- 1980-08-28 NL NLAANVRAGE8004873,A patent/NL183080C/xx not_active IP Right Cessation
- 1980-08-29 NO NO802563A patent/NO156010C/no unknown
- 1980-08-29 JP JP55119632A patent/JPS5923313B2/ja not_active Expired
- 1980-08-29 ES ES494668A patent/ES8106513A1/es not_active Expired
- 1980-08-29 IE IE1823/80A patent/IE50231B1/en unknown
- 1980-08-29 CA CA000359284A patent/CA1172259A/en not_active Expired
- 1980-08-29 FR FR8018813A patent/FR2464262A1/fr active Granted
-
1984
- 1984-01-20 JP JP59007386A patent/JPS5946947B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2057437A (en) | 1981-04-01 |
| NO802563L (no) | 1981-03-02 |
| GB2057437B (en) | 1984-08-30 |
| IT1193979B (it) | 1988-08-31 |
| FR2464262B1 (enExample) | 1983-07-08 |
| ES494668A0 (es) | 1981-08-16 |
| FI72724B (fi) | 1987-03-31 |
| NL183080C (nl) | 1988-07-18 |
| CA1172259A (en) | 1984-08-07 |
| ES8106513A1 (es) | 1981-08-16 |
| JPS59144779A (ja) | 1984-08-18 |
| BE884743A (fr) | 1980-12-01 |
| FI802652A7 (fi) | 1981-03-01 |
| GR69849B (enExample) | 1982-07-19 |
| NO156010B (no) | 1987-03-30 |
| DK153948B (da) | 1988-09-26 |
| JPS5655386A (en) | 1981-05-15 |
| SE448455B (sv) | 1987-02-23 |
| ATA432080A (de) | 1983-02-15 |
| FI72724C (fi) | 1987-07-10 |
| IE50231B1 (en) | 1986-03-05 |
| FR2464262A1 (fr) | 1981-03-06 |
| AT372381B (de) | 1983-09-26 |
| DE3031710C2 (de) | 1987-03-12 |
| CH646412A5 (fr) | 1984-11-30 |
| US4285964A (en) | 1981-08-25 |
| DE3031710A1 (de) | 1981-03-12 |
| IT8024310A0 (it) | 1980-08-27 |
| NL8004873A (nl) | 1981-03-03 |
| NO156010C (no) | 1987-07-08 |
| JPS5946947B2 (ja) | 1984-11-15 |
| IE801823L (en) | 1981-02-28 |
| DK358980A (da) | 1981-03-01 |
| DK153948C (da) | 1989-02-13 |
| SE8005890L (sv) | 1981-03-01 |
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