CH390231A - Verfahren zur Herstellung eines Sennosid-Komplexes - Google Patents

Verfahren zur Herstellung eines Sennosid-Komplexes

Info

Publication number: CH390231A
Authority: CH; Switzerland
Prior art keywords: sennoside; complex; sennosides; polymeric carbohydrate; preparation
Prior art date: 1959-07-16

Application number

CH7603259A

Other languages

German (de)

English (en)

Inventor

Halpern Alfred

Original Assignee

Mundipharma Ag

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.)

1959-07-16

Filing date

1959-07-21

Publication date

1965-04-15

1959-07-16 Priority to DEM42151A priority Critical patent/DE1172655B/de

1959-07-21 Application filed by Mundipharma Ag filed Critical Mundipharma Ag

1959-07-21 Priority to CH7603259A priority patent/CH390231A/de

1959-07-27 Priority to FR801205A priority patent/FR1042M/fr

1959-07-30 Priority to BE581227A priority patent/BE581227A/fr

1965-04-15 Publication of CH390231A publication Critical patent/CH390231A/de

Links

229930186851 sennoside Natural products 0.000 title claims description 30
229940124513 senna glycoside Drugs 0.000 title claims description 18
IPQVTOJGNYVQEO-KGFNBKMBSA-N sennoside A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1[C@@H]2[C@H]1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-KGFNBKMBSA-N 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title description 5
IPQVTOJGNYVQEO-UHFFFAOYSA-N 9-[2-carboxy-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9h-anthracen-9-yl]-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9h-anthracene-2-carboxylic acid Chemical class OC1C(O)C(O)C(CO)OC1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1C2C1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(OC3C(C(O)C(O)C(CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-UHFFFAOYSA-N 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
150000001720 carbohydrates Chemical class 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
239000000783 alginic acid Substances 0.000 claims description 5
235000010443 alginic acid Nutrition 0.000 claims description 5
229920000615 alginic acid Polymers 0.000 claims description 5
229960001126 alginic acid Drugs 0.000 claims description 5
150000004781 alginic acids Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229920002230 Pectic acid Polymers 0.000 claims description 4
239000010318 polygalacturonic acid Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
229920002907 Guar gum Polymers 0.000 claims 1
239000000665 guar gum Substances 0.000 claims 1
235000010417 guar gum Nutrition 0.000 claims 1
229960002154 guar gum Drugs 0.000 claims 1
239000001133 paullinia cupana hbk gum Substances 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
241001249696 Senna alexandrina Species 0.000 description 9
238000000502 dialysis Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000829 suppository Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JQVYZJIFFAHQKX-ZAULLPPESA-L calcium;3-carboxy-10-[2-carboxy-4-oxido-10-oxo-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9h-anthracen-9-yl]-9-oxo-8-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10h-anthracen-1-olate Chemical compound [Ca+2].O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C([O-])=O)C=C1C2C1C2=CC(C([O-])=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 JQVYZJIFFAHQKX-ZAULLPPESA-L 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000009814 sennoside A&B Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
229930182478 glucoside Natural products 0.000 description 3
150000008131 glucosides Chemical class 0.000 description 3
229930182470 glycoside Natural products 0.000 description 3
150000002338 glycosides Chemical class 0.000 description 3
239000012528 membrane Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000011389 fruit/vegetable juice Nutrition 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
210000002429 large intestine Anatomy 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
IPQVTOJGNYVQEO-CXZNLNCXSA-N sennoside A Natural products O=C(O)c1cc(O)c2C(=O)c3c(O[C@H]4[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O4)cccc3[C@@H]([C@H]3c4c(c(O)cc(C(=O)O)c4)C(=O)c4c(O[C@H]5[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O5)cccc34)c2c1 IPQVTOJGNYVQEO-CXZNLNCXSA-N 0.000 description 2
235000006693 Cassia laevigata Nutrition 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000011149 active material Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000003249 myenteric plexus Anatomy 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
IPQVTOJGNYVQEO-JLDSCGAUSA-N sennoside Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1C2C1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-JLDSCGAUSA-N 0.000 description 1
IPQVTOJGNYVQEO-AIFLABODSA-N sennoside B Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1[C@H]2[C@H]1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-AIFLABODSA-N 0.000 description 1
229940004991 sennoside b Drugs 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical group N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
238000005303 weighing Methods 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
- C07H15/244—Anthraquinone radicals, e.g. sennosides
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7012—Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/734—Alginic acid
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/736—Glucomannans or galactomannans, e.g. locust bean gum, guar gum
- 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)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- 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)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K36/482—Cassia, e.g. golden shower tree

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Natural Medicines & Medicinal Plants (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Botany (AREA)
Organic Chemistry (AREA)
Alternative & Traditional Medicine (AREA)
Medical Informatics (AREA)
Microbiology (AREA)
Mycology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

CH7603259A 1959-07-16 1959-07-21 Verfahren zur Herstellung eines Sennosid-Komplexes CH390231A (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
DEM42151A DE1172655B (de)	1959-07-16	1959-07-16	Verfahren zur Herstellung von als verbesserte Abfuehrmittel verwendbaren Sennosid-Molekular-komplexen mit Polysacchariden
CH7603259A CH390231A (de)	1959-07-16	1959-07-21	Verfahren zur Herstellung eines Sennosid-Komplexes
FR801205A FR1042M (fr)	1959-07-16	1959-07-27
BE581227A BE581227A (fr)	1959-07-16	1959-07-30	Complexe sennoside-polymere carbohydraté

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DEM42151A DE1172655B (de)	1959-07-16	1959-07-16	Verfahren zur Herstellung von als verbesserte Abfuehrmittel verwendbaren Sennosid-Molekular-komplexen mit Polysacchariden
CH7603259A CH390231A (de)	1959-07-16	1959-07-21	Verfahren zur Herstellung eines Sennosid-Komplexes
FR801205A FR1042M (fr)	1959-07-16	1959-07-27

Publications (1)

Publication Number	Publication Date
CH390231A true CH390231A (de)	1965-04-15

Family

ID=55527940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7603259A CH390231A (de)	1959-07-16	1959-07-21	Verfahren zur Herstellung eines Sennosid-Komplexes

Country Status (4)

Country	Link
BE (1)	BE581227A (fr)
CH (1)	CH390231A (fr)
DE (1)	DE1172655B (fr)
FR (1)	FR1042M (fr)

1959
- 1959-07-16 DE DEM42151A patent/DE1172655B/de active Pending
- 1959-07-21 CH CH7603259A patent/CH390231A/de unknown
- 1959-07-27 FR FR801205A patent/FR1042M/fr not_active Expired
- 1959-07-30 BE BE581227A patent/BE581227A/fr unknown

Also Published As

Publication number	Publication date
FR1042M (fr)	1962-02-09
DE1172655B (de)	1964-06-25
BE581227A (fr)	1960-02-01

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