CA1049497A - Aesculus-saponine and salts - Google Patents
Aesculus-saponine and saltsInfo
- Publication number
- CA1049497A CA1049497A CA256,649A CA256649A CA1049497A CA 1049497 A CA1049497 A CA 1049497A CA 256649 A CA256649 A CA 256649A CA 1049497 A CA1049497 A CA 1049497A
- Authority
- CA
- Canada
- Prior art keywords
- escin
- eluate
- separating
- seeds
- methanol
- 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
- 150000003839 salts Chemical class 0.000 title claims description 9
- 229940011399 escin Drugs 0.000 claims abstract description 52
- 229930186222 escin Natural products 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000001768 cations Chemical class 0.000 claims abstract description 12
- 235000010181 horse chestnut Nutrition 0.000 claims abstract description 11
- 241000157280 Aesculus hippocastanum Species 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 241000157282 Aesculus Species 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical group O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000000638 solvent extraction Methods 0.000 claims 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 10
- 230000001741 anti-phlogistic effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 18
- 229940079593 drug Drugs 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SYXUBXTYGFJFEH-UHFFFAOYSA-N oat triterpenoid saponin Chemical compound CNC1=CC=CC=C1C(=O)OC1C(C=O)(C)CC2C3(C(O3)CC3C4(CCC5C(C)(CO)C(OC6C(C(O)C(OC7C(C(O)C(O)C(CO)O7)O)CO6)OC6C(C(O)C(O)C(CO)O6)O)CCC53C)C)C4(C)CC(O)C2(C)C1 SYXUBXTYGFJFEH-UHFFFAOYSA-N 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000034656 Contusions Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009519 contusion Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940075894 denatured ethanol Drugs 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000002980 postoperative effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 208000000104 Arthus reaction Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010008334 Cervicobrachial syndrome Diseases 0.000 description 1
- 206010010254 Concussion Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 108010003272 Hyaluronate lyase Proteins 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 206010039203 Road traffic accident Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- 206010053614 Type III immune complex mediated reaction Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000369 acute toxicity data Toxicity 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003659 bee venom Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 231100001048 fetal toxicity Toxicity 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003716 mesoderm Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002223 polystyrene Polymers 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2530941A DE2530941C2 (de) | 1975-07-11 | 1975-07-11 | Verfahren zur Gewinnung von kristallinem Aescin und zur Herstellung von bestimmten Aescin-Salzen sowie Triethanolammoniumaescinat und dieses Salz enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049497A true CA1049497A (en) | 1979-02-27 |
Family
ID=5951217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,649A Expired CA1049497A (en) | 1975-07-11 | 1976-07-09 | Aesculus-saponine and salts |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5234913A (cs) |
| AR (1) | AR210498A1 (cs) |
| AU (1) | AU510202B2 (cs) |
| BE (1) | BE844052A (cs) |
| BG (1) | BG27378A3 (cs) |
| CA (1) | CA1049497A (cs) |
| CS (1) | CS193077B2 (cs) |
| DE (1) | DE2530941C2 (cs) |
| ES (1) | ES449747A1 (cs) |
| FI (1) | FI63418C (cs) |
| FR (1) | FR2316962A1 (cs) |
| GB (1) | GB1551387A (cs) |
| HK (1) | HK33781A (cs) |
| HU (1) | HU175394B (cs) |
| PH (1) | PH13088A (cs) |
| PL (1) | PL99027B1 (cs) |
| PT (1) | PT65301B (cs) |
| RO (1) | RO71026A (cs) |
| SU (1) | SU786856A3 (cs) |
| YU (1) | YU39215B (cs) |
| ZA (1) | ZA764064B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0205771A (pt) * | 2002-03-25 | 2004-01-13 | Council Scient Ind Res | Processo simples para obtenção de (beta)-aescina a partir de castanha de cavalo indiano (aesculus indica) |
| RU2290189C1 (ru) * | 2005-06-17 | 2006-12-27 | Игорь Юрьевич Макаров | Средство, обладающее венотонизирующим, противовоспалительным и капилляропротекторным действием, и способ его получения |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1095989B (de) * | 1959-03-11 | 1960-12-29 | Madaus & Co Dr | Verfahren zur Gewinnung eines kristallisierten sauren Saponins aus dem Samen der Rosskastanie |
| FR1267224A (fr) * | 1960-06-07 | 1961-07-21 | Madaus & Co Dr | Procédé de préparation de saponine acide cristallisée à partir de marrons d'inde |
| DE1667884B2 (de) * | 1968-01-20 | 1976-09-30 | Knoll Ag, Chemische Fabriken, 6700 Ludwigshafen | Verfahren zur gewinnung von reinem aescin |
| DE2118916A1 (en) * | 1971-04-19 | 1972-11-09 | Schwabe, Willmar, Dr., 7500 Karlsruhe-Durlach | Water-soluble acid saponin mixts prodn - by extraction of horse-chestnuts and complex formation with (alkyl)benzene |
| YU37063B (en) * | 1971-12-06 | 1984-08-31 | Lek Tovarna Farmacevtskih | Process for preparing x-ray amorphous water-sulubleascin |
-
1975
- 1975-07-11 DE DE2530941A patent/DE2530941C2/de not_active Expired - Lifetime
-
1976
- 1976-06-23 AR AR263714A patent/AR210498A1/es active
- 1976-06-30 PT PT65301A patent/PT65301B/pt unknown
- 1976-07-05 BG BG033672A patent/BG27378A3/xx unknown
- 1976-07-05 FI FI761957A patent/FI63418C/fi not_active IP Right Cessation
- 1976-07-07 GB GB28232/76A patent/GB1551387A/en not_active Expired
- 1976-07-07 SU SU762377644A patent/SU786856A3/ru active
- 1976-07-08 YU YU01669/76A patent/YU39215B/xx unknown
- 1976-07-08 ZA ZA764064A patent/ZA764064B/xx unknown
- 1976-07-08 AU AU15730/76A patent/AU510202B2/en not_active Expired
- 1976-07-09 CA CA256,649A patent/CA1049497A/en not_active Expired
- 1976-07-09 HU HU76MA2796A patent/HU175394B/hu not_active IP Right Cessation
- 1976-07-09 CS CS764568A patent/CS193077B2/cs unknown
- 1976-07-10 RO RO7686933A patent/RO71026A/ro unknown
- 1976-07-10 PL PL1976191113A patent/PL99027B1/pl unknown
- 1976-07-10 ES ES449747A patent/ES449747A1/es not_active Expired
- 1976-07-12 BE BE168848A patent/BE844052A/xx not_active IP Right Cessation
- 1976-07-12 FR FR7621314A patent/FR2316962A1/fr active Granted
- 1976-07-12 PH PH18679A patent/PH13088A/en unknown
- 1976-07-12 JP JP51082845A patent/JPS5234913A/ja active Granted
-
1981
- 1981-07-16 HK HK337/81A patent/HK33781A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU39215B (en) | 1984-08-31 |
| AU510202B2 (en) | 1980-06-12 |
| RO71026A (ro) | 1981-09-24 |
| SU786856A3 (ru) | 1980-12-07 |
| BG27378A3 (bg) | 1979-10-12 |
| PH13088A (en) | 1979-11-23 |
| ES449747A1 (es) | 1977-08-16 |
| PT65301B (de) | 1977-12-13 |
| BE844052A (fr) | 1977-01-12 |
| YU166976A (en) | 1982-08-31 |
| CS193077B2 (en) | 1979-09-17 |
| FR2316962B1 (cs) | 1979-03-02 |
| DE2530941A1 (de) | 1977-01-27 |
| PT65301A (de) | 1976-07-01 |
| ZA764064B (en) | 1977-07-27 |
| DE2530941C2 (de) | 1991-10-10 |
| GB1551387A (en) | 1979-08-30 |
| FI63418C (fi) | 1983-06-10 |
| FR2316962A1 (fr) | 1977-02-04 |
| FI63418B (fi) | 1983-02-28 |
| HK33781A (en) | 1981-07-24 |
| JPS5539560B2 (cs) | 1980-10-13 |
| HU175394B (hu) | 1980-07-28 |
| AR210498A1 (es) | 1977-08-15 |
| PL99027B1 (pl) | 1978-06-30 |
| JPS5234913A (en) | 1977-03-17 |
| FI761957A7 (cs) | 1977-01-12 |
| AU1573076A (en) | 1978-01-12 |
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