CA1049497A - Aesculus-saponine et sels derives - Google Patents

Aesculus-saponine et sels derives

Info

Publication number: CA1049497A
Authority: CA; Canada
Prior art keywords: escin; eluate; separating; seeds; methanol
Prior art date: 1975-07-11
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

Application number

CA256,649A

Other languages

English (en)

Inventor

Rolf Madaus

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Madaus Holding GmbH

Original Assignee

Dr Madaus GmbH and Co

Priority date (The priority date 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 date listed.)

1975-07-11

Filing date

1976-07-09

Publication date

1979-02-27

1976-07-09 Application filed by Dr Madaus GmbH and Co filed Critical Dr Madaus GmbH and Co

1979-02-27 Application granted granted Critical

1979-02-27 Publication of CA1049497A publication Critical patent/CA1049497A/fr

Status Expired legal-status Critical Current

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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (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)

CA256,649A 1975-07-11 1976-07-09 Aesculus-saponine et sels derives Expired CA1049497A (fr)

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 (fr)	1979-02-27

Family

ID=5951217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA256,649A Expired CA1049497A (fr)	1975-07-11	1976-07-09	Aesculus-saponine et sels derives

Country Status (21)

Country	Link
JP (1)	JPS5234913A (fr)
AR (1)	AR210498A1 (fr)
AU (1)	AU510202B2 (fr)
BE (1)	BE844052A (fr)
BG (1)	BG27378A3 (fr)
CA (1)	CA1049497A (fr)
CS (1)	CS193077B2 (fr)
DE (1)	DE2530941C2 (fr)
ES (1)	ES449747A1 (fr)
FI (1)	FI63418C (fr)
FR (1)	FR2316962A1 (fr)
GB (1)	GB1551387A (fr)
HK (1)	HK33781A (fr)
HU (1)	HU175394B (fr)
PH (1)	PH13088A (fr)
PL (1)	PL99027B1 (fr)
PT (1)	PT65301B (fr)
RO (1)	RO71026A (fr)
SU (1)	SU786856A3 (fr)
YU (1)	YU39215B (fr)
ZA (1)	ZA764064B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003080636A1 (fr) *	2002-03-25	2003-10-02	Council Of Scientific And Industrial Research	Processus simple d'obtention de beta-aescine a partir de marronnier de l'himalaya (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)

* Cited by examiner, † Cited by third party
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 AU AU15730/76A patent/AU510202B2/en not_active Expired
- 1976-07-08 YU YU01669/76A patent/YU39215B/xx unknown
- 1976-07-08 ZA ZA764064A patent/ZA764064B/xx unknown
- 1976-07-09 CA CA256,649A patent/CA1049497A/fr not_active Expired
- 1976-07-09 CS CS764568A patent/CS193077B2/cs unknown
- 1976-07-09 HU HU76MA2796A patent/HU175394B/hu not_active IP Right Cessation
- 1976-07-10 PL PL1976191113A patent/PL99027B1/pl unknown
- 1976-07-10 RO RO7686933A patent/RO71026A/fr unknown
- 1976-07-10 ES ES449747A patent/ES449747A1/es not_active Expired
- 1976-07-12 PH PH18679A patent/PH13088A/en unknown
- 1976-07-12 JP JP51082845A patent/JPS5234913A/ja active Granted
- 1976-07-12 FR FR7621314A patent/FR2316962A1/fr active Granted
- 1976-07-12 BE BE168848A patent/BE844052A/fr not_active IP Right Cessation
1981
- 1981-07-16 HK HK337/81A patent/HK33781A/xx unknown

Also Published As

Publication number	Publication date
FI761957A7 (fr)	1977-01-12
FR2316962B1 (fr)	1979-03-02
FR2316962A1 (fr)	1977-02-04
YU39215B (en)	1984-08-31
BG27378A3 (bg)	1979-10-12
HK33781A (en)	1981-07-24
ZA764064B (en)	1977-07-27
AU510202B2 (en)	1980-06-12
AU1573076A (en)	1978-01-12
JPS5539560B2 (fr)	1980-10-13
SU786856A3 (ru)	1980-12-07
ES449747A1 (es)	1977-08-16
PT65301A (de)	1976-07-01
DE2530941C2 (de)	1991-10-10
FI63418C (fi)	1983-06-10
BE844052A (fr)	1977-01-12
JPS5234913A (en)	1977-03-17
PT65301B (de)	1977-12-13
GB1551387A (en)	1979-08-30
YU166976A (en)	1982-08-31
HU175394B (hu)	1980-07-28
DE2530941A1 (de)	1977-01-27
PL99027B1 (pl)	1978-06-30
PH13088A (en)	1979-11-23
CS193077B2 (en)	1979-09-17
AR210498A1 (es)	1977-08-15
FI63418B (fi)	1983-02-28
RO71026A (fr)	1981-09-24

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CA1049497A (fr)	1979-02-27	Aesculus-saponine et sels derives
DE2323746C2 (de)	1987-04-30	Estersalze der 2,5-Dihydroxybenzolsulfonsäure, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
RU2088256C1 (ru)	1997-08-27	Средство для комплексной терапии заболеваний "диквертин" и способ его получения
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US3163636A (en)	1964-12-29	Genuine escin from horse chestnut extracts, and process of producing same
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