DD210277A5 - Verfahren zur herstellung von physiologisch aktive pterocarpanverbindungen - Google Patents

Verfahren zur herstellung von physiologisch aktive pterocarpanverbindungen Download PDF

Info

Publication number: DD210277A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; fraction; aqueous; methanol; compounds
Prior art date: 1982-03-15

Application number

DD83248826A

Other languages

German (de)

English (en)

Inventor

Laszlo L Darko

Koji Nakanishi

Masashi Nakagawa

Original Assignee

Richter Gedeon Vegyeszet

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.)

1982-03-15

Filing date

1983-03-15

Publication date

1984-06-06

1982-03-15 Priority claimed from US06/357,805 external-priority patent/US4429141A/en

1982-03-15 Priority claimed from US06/358,191 external-priority patent/US4443472A/en

1983-03-15 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1984-06-06 Publication of DD210277A5 publication Critical patent/DD210277A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 23
230000008569 process Effects 0.000 title claims abstract description 8
LZEPVVDVBJUKSG-UHFFFAOYSA-N pterocarpan Chemical class C1=CC=C2C3COC4=CC=CC=C4C3OC2=C1 LZEPVVDVBJUKSG-UHFFFAOYSA-N 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 44
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 14
239000012675 alcoholic extract Substances 0.000 claims abstract description 4
239000008346 aqueous phase Substances 0.000 claims abstract description 3
238000004587 chromatography analysis Methods 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000012071 phase Substances 0.000 claims description 8
238000004128 high performance liquid chromatography Methods 0.000 claims description 7
239000000287 crude extract Substances 0.000 claims description 6
239000003480 eluent Substances 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000002158 endotoxin Substances 0.000 abstract description 7
241000238631 Hexapoda Species 0.000 abstract description 5
241000270295 Serpentes Species 0.000 abstract description 5
231100000611 venom Toxicity 0.000 abstract description 5
231100000614 poison Toxicity 0.000 abstract description 4
241000588724 Escherichia coli Species 0.000 abstract description 3
231100000331 toxic Toxicity 0.000 abstract description 3
230000002588 toxic effect Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
239000002574 poison Substances 0.000 abstract description 2
241000239290 Araneae Species 0.000 abstract 1
230000000694 effects Effects 0.000 description 22
241001465754 Metazoa Species 0.000 description 17
239000003998 snake venom Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000029058 respiratory gaseous exchange Effects 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
208000005374 Poisoning Diseases 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
231100000572 poisoning Toxicity 0.000 description 7
230000000607 poisoning effect Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000000729 antidote Substances 0.000 description 6
231100000636 lethal dose Toxicity 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000003053 toxin Substances 0.000 description 6
231100000765 toxin Toxicity 0.000 description 6
108700012359 toxins Proteins 0.000 description 6
241000271511 Bothrops atrox Species 0.000 description 5
210000003169 central nervous system Anatomy 0.000 description 5
239000003937 drug carrier Substances 0.000 description 5
230000006870 function Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000002560 therapeutic procedure Methods 0.000 description 5
230000004872 arterial blood pressure Effects 0.000 description 4
230000036772 blood pressure Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000002156 mixing Methods 0.000 description 4
210000005036 nerve Anatomy 0.000 description 4
230000002232 neuromuscular Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000271538 Crotalus durissus Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000008859 change Effects 0.000 description 3
230000008602 contraction Effects 0.000 description 3
230000036540 impulse transmission Effects 0.000 description 3
230000035987 intoxication Effects 0.000 description 3
231100000566 intoxication Toxicity 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
231100000699 Bacterial toxin Toxicity 0.000 description 2
208000003508 Botulism Diseases 0.000 description 2
206010009192 Circulatory collapse Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
208000010476 Respiratory Paralysis Diseases 0.000 description 2
230000036982 action potential Effects 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000002605 anti-dotal effect Effects 0.000 description 2
239000000688 bacterial toxin Substances 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000003304 gavage Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
230000001717 pathogenic effect Effects 0.000 description 2
230000007096 poisonous effect Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000002435 venom Substances 0.000 description 2
210000001048 venom Anatomy 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
108030001720 Bontoxilysin Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000193155 Clostridium botulinum Species 0.000 description 1
241000271532 Crotalus Species 0.000 description 1
241000271537 Crotalus atrox Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010016952 Food poisoning Diseases 0.000 description 1
208000019331 Foodborne disease Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
206010038687 Respiratory distress Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
230000009471 action Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000001166 anti-perspirative effect Effects 0.000 description 1
239000003213 antiperspirant Substances 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229940053031 botulinum toxin Drugs 0.000 description 1
230000007177 brain activity Effects 0.000 description 1
-1 carbon aliphatic hydrocarbon Chemical class 0.000 description 1
231100000457 cardiotoxic Toxicity 0.000 description 1
230000001451 cardiotoxic effect Effects 0.000 description 1
230000009084 cardiovascular function Effects 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
238000001142 circular dichroism spectrum Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000000179 crotalid venom Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
231100000776 exotoxin Toxicity 0.000 description 1
239000002095 exotoxin Substances 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
231100000189 neurotoxic Toxicity 0.000 description 1
230000002887 neurotoxic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
239000003186 pharmaceutical solution Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
230000005801 respiratory difficulty Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)

DD83248826A 1982-03-15 1983-03-15 Verfahren zur herstellung von physiologisch aktive pterocarpanverbindungen DD210277A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/357,805 US4429141A (en)	1982-03-15	1982-03-15	Physiologically active compounds and their isolation
US06/358,191 US4443472A (en)	1982-03-15	1982-03-15	Method of treating mammals for effects of neuro- and cardiovascular toxins

Publications (1)

Publication Number	Publication Date
DD210277A5 true DD210277A5 (de)	1984-06-06

Family

ID=26999801

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD83248826A DD210277A5 (de)	1982-03-15	1983-03-15	Verfahren zur herstellung von physiologisch aktive pterocarpanverbindungen
DD83260100A DD216464A5 (de)	1982-03-15	1983-03-15	Verfahren zur isolierung von physiologisch aktiven pterocarpan-verbindungen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD83260100A DD216464A5 (de)	1982-03-15	1983-03-15	Verfahren zur isolierung von physiologisch aktiven pterocarpan-verbindungen

Country Status (11)

Country	Link
EP (1)	EP0089229B1 (pl)
AU (1)	AU560343B2 (pl)
CA (1)	CA1179357A (pl)
DD (2)	DD210277A5 (pl)
DE (1)	DE3366925D1 (pl)
DK (1)	DK90483A (pl)
FI (1)	FI79320C (pl)
HU (1)	HU187499B (pl)
IL (1)	IL68016A0 (pl)
NO (1)	NO153731C (pl)
PL (1)	PL140870B1 (pl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU6886896A (en) *	1996-08-28	1998-03-19	Farmacon, Inc.	Phenylbutanol derivatives, methods for their preparation and pharmaceutical compositions thereof
BRPI0806047A2 (pt) *	2008-11-06	2010-09-14	Univ Rio De Janeiro	novos compostos da famìlia das pterocarpaquinonas, processo de produção, composição farmacêutica contendo os novos compostos da famìlia das pterocarpaquinonas, usos e método terapêutico

1983
- 1983-02-25 DK DK90483A patent/DK90483A/da not_active Application Discontinuation
- 1983-03-01 IL IL68016A patent/IL68016A0/xx not_active IP Right Cessation
- 1983-03-09 CA CA000423160A patent/CA1179357A/en not_active Expired
- 1983-03-10 FI FI830811A patent/FI79320C/fi not_active IP Right Cessation
- 1983-03-11 HU HU83844A patent/HU187499B/hu not_active IP Right Cessation
- 1983-03-11 AU AU12429/83A patent/AU560343B2/en not_active Ceased
- 1983-03-14 PL PL1983241020A patent/PL140870B1/pl unknown
- 1983-03-14 NO NO830889A patent/NO153731C/no unknown
- 1983-03-15 EP EP83301424A patent/EP0089229B1/en not_active Expired
- 1983-03-15 DD DD83248826A patent/DD210277A5/de not_active IP Right Cessation
- 1983-03-15 DD DD83260100A patent/DD216464A5/de not_active IP Right Cessation
- 1983-03-15 DE DE8383301424T patent/DE3366925D1/de not_active Expired

Also Published As

Publication number	Publication date
EP0089229A3 (en)	1984-05-02
DK90483A (da)	1983-09-16
PL140870B1 (en)	1987-06-30
EP0089229B1 (en)	1986-10-15
DD216464A5 (de)	1984-12-12
DK90483D0 (da)	1983-02-25
NO830889L (no)	1983-09-16
FI830811A0 (fi)	1983-03-10
PL241020A1 (en)	1984-07-30
EP0089229A2 (en)	1983-09-21
AU560343B2 (en)	1987-04-02
AU1242983A (en)	1983-09-22
HU187499B (en)	1986-01-28
NO153731C (no)	1986-05-14
FI830811L (fi)	1983-09-16
CA1179357A (en)	1984-12-11
DE3366925D1 (en)	1986-11-20
FI79320B (fi)	1989-08-31
IL68016A0 (en)	1983-06-15
FI79320C (fi)	1989-12-11
NO153731B (no)	1986-02-03

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

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EP0599307B1 (de)	1998-08-26	Johanniskraut-Trockenextrakt, Verfahren zu seiner Herstellung und seine Verwendung
EP0501205B1 (de)	1995-05-24	Antiphlogistisches Mittel
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