US3689516A - Bis-carboxyethyl germanium sesquioxide and process for preparing same - Google Patents
Bis-carboxyethyl germanium sesquioxide and process for preparing same Download PDFInfo
- Publication number
- US3689516A US3689516A US805370A US3689516DA US3689516A US 3689516 A US3689516 A US 3689516A US 805370 A US805370 A US 805370A US 3689516D A US3689516D A US 3689516DA US 3689516 A US3689516 A US 3689516A
- Authority
- US
- United States
- Prior art keywords
- bis
- germanium sesquioxide
- trichlorogermanium
- compound
- carboxyethyl germanium
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/30—Germanium compounds
Definitions
- the compound of the invention inhibits the proliferation of Ehrlich ascites tumor cells.
- Germanium which has the atomic number of 32, is an atom having 32 electrons. Four of these electrons are located in an outer orbit and are unstable, being capable of separation from the rest under certain conditions. This property of germanium is utilized for transistors or diode rectifiers, as is popularly known. And there is a phenomenon that, when one of these four electrons has escaped, there results what is referred to as a positive hole of electric potential, to which other nearby electrons are drawn in. The composition of germanium being so, its organic compound is apt to cause electric charge transfer and to generate organic free radicals.
- Applicants have for a long time studied the components of plant substances used for the so-called Chinese medical herbs, which have been known to be effective to check abnormal cells in the living body, and discovered that they contained a very large content of germanium, for example, 320 ppm in ginseng, 257 ppm in water-caltrop nut, 124 ppm in box-thorn nut, 108 ppm in wisteriaknot, 50 ppm in pearlbarley seed, 58 ppm in erythrorhizon, 76 ppm in comfry, and 756 ppm in garlic. This fact appears to indicate that germanium exists within these plants in the form of organic compounds.
- B-cyanoethyltrichlorogermanium trichlorogermanium ethylene cyanide is obtained by the action of acrylonitrile on the known compound trichlorogermanium (germaniumchloroform).
- B-Cyanoethyltrichlorogermanium is converted into B- trichlorogermanium propionic acid (trichlorogermanium propionic acid) by hydrolysis in the presence of a mineral acid and by the action of thionylchloride, this latter compound is converted to trichlorogermanium propionyl chloride. Hydrolysis of this compound with water produces bis-carboxylethyl germanium sesquioxide.
- Test mice DD Shizuoka, 4 weeks old.
- the administered group were very vigorous and had good appetite compared with the control group, showing no external appearance of reaction, the control group showed stagnant ascites whereas the administered group showed neither ascites stagnation nor bleeding, the proportion of the number of tumor cells in the bodies of the administered group was approximately 26 percent against percent in the bodies of the control group, and that there was a good indication of the effective checking of fissiparism.
- the compound, bis-carboxyethyl germanium sesquioxide is a, are white, crystalline powder, and capable of polymerization on heating. Its melting point is impossible to measure, since heating to a higher temperature causes decomposition. In water solution, the oxygen in germanium sesquioxide is hydrated and the hydrogen stimulates charge transfer, thus causing activation. 7
- the novel compound according to the present invention is of a very low order of toxicity.
- the LD in mice as determined by hypodermic injection is 3,5g/kg of body weight.
- the compound of the invention is soluble in water, and therefore it is most convenient to formulate it as solutions in sterile, pyrogen-free water, although any pharmaceutically acceptable carrier may be used.
- a preferred therapeutic composition of the invention will comprise an aqueous solution containing from 0.01 to 0.4 by weight of the active ingredient.
- compositions containing the compound according to the invention can be administered orally or Number of E.A.'I. Ascites amount, Aver- '1.I.,
- Example l To 18 gr. of germaniumchloroform are added 6 gr. of acrylonitrile, and by heating under an atmosphere of 55 nitrogengas, Byanoethyltrichlorogermanium is obtained. This is converted to B-trichlorogermanium propionic acid by adding hydrochloric acid solution and heating. This is converted through reaction upon the dropwise addition of 12 gr. of thionylchloride, to trichlorogermanium propionyl chloride, which is recovered by distillation in vacuo. After complete hydrolysis takes place with water, bis-carboxyethyl germanium sesquioxide is obtained. This is washed with water until chlorine reaction disappears and a white powder is obtained. The yield is about 6 gr. Anal. calcd. for C,l-l ,O,(I1E Calculated value: 1 H2294, Ge:42.64 Found 113.00, Ge:42.41
- the carrier can be a solid and in the form of a powder or tablet.
- the solid carrier can be any of those commonly used in making medicinal formulations.
Abstract
The compound bis-carboxyethyl germanium sesquioxide is prepared as illustrated by the following equations:
Description
United States Patent Asai et al.
[ Sept. 5, 1972 [72] Inventors: Kazuhiko Asai, Tokyo-to; Kazuo Makabe, Kamakura-shi, both of Japan [73] Assignee: Daiichi Yakuhin Sangyo Kabushiki Kaisha, Tokyo-to, Japan [22] Filed: March 7, 1969 [21] Appl. No.: 805,370
[30] Foreign Application Priority Data March 29, 1968 Japan ..43/200s5 [52] US. Cl. ..260/429 R, 424/287 [51] Int. Cl. ..C07j 7/00, A6lk 27/00 [58] Field of Search ..260/429 [56] References Cited OTHER PUBLICATIONS Lesbre et al. Compt. Rend. Vol. 247 (1958) p. 471- Primary Examiner-Delbert E. Gantz Assistant ExaminerA. P. Dem'ers Attorney-Scrivener, Parker, Scrivener and Clarke ABSTRACT The compound bis-carboxyethyl germanium sesquioxide is prepared as illustrated by the following equations:
GeIIClg CIIgzCHCN Cl Gn-Cll Cll' CN Hydrolysis Cl3Ge-CII2CIIzCN ChGeCIhCIhCOOlI Hydrolysis 2C1; GeCHzCHzC 0 C1 This compound is effective for inhibiting the proliferation of Ehrlich ascites tumor cells.
2 Claims, No Drawings BIS-CARBOXYETI'IYL GERMANIUM SESQUIOXIDE AND PROCESS FOR PREPARING SAME DETAILED EXPLANATION OF THE INVENTION This invention relates to the compound bis-carboxyethyl germanium sesquioxide and having the following formula:
This is a compound and the invention also relates to a process of preparing it.
The compound of the invention inhibits the proliferation of Ehrlich ascites tumor cells.
It is believed that the mechanism by which the compound of the invention operates, is derived from the fact, already known, that the electric potential of abnormal cells in the living body is different from thatof normal cells.
Germanium, which has the atomic number of 32, is an atom having 32 electrons. Four of these electrons are located in an outer orbit and are unstable, being capable of separation from the rest under certain conditions. This property of germanium is utilized for transistors or diode rectifiers, as is popularly known. And there is a phenomenon that, when one of these four electrons has escaped, there results what is referred to as a positive hole of electric potential, to which other nearby electrons are drawn in. The composition of germanium being so, its organic compound is apt to cause electric charge transfer and to generate organic free radicals.
Applicants have for a long time studied the components of plant substances used for the so-called Chinese medical herbs, which have been known to be effective to check abnormal cells in the living body, and discovered that they contained a very large content of germanium, for example, 320 ppm in ginseng, 257 ppm in water-caltrop nut, 124 ppm in box-thorn nut, 108 ppm in wisteriaknot, 50 ppm in pearlbarley seed, 58 ppm in erythrorhizon, 76 ppm in comfry, and 756 ppm in garlic. This fact appears to indicate that germanium exists within these plants in the form of organic compounds.
The presence of this property of germanium and its peculiar characteristics previously described, led applicant to conclude that, if an organic germanium compound could be found that has the property to absorb a nearby electron, due to the escape of an electron resulting in a positive hole of electric potential, it could be utilized to change the electric potential of abnormal cells in the living body and to check their proliferation, it being known that the electric potential of abnormal cells is different from that of normal cells. Extensive research on the activities of various germanium compounds then followed. As a result, it was discovered that this activity is displayed by the compound of the invention, and this discovery led to the invention.
The process of making the compound according to the invention is as follows: B-cyanoethyltrichlorogermanium trichlorogermanium ethylene cyanide) is obtained by the action of acrylonitrile on the known compound trichlorogermanium (germaniumchloroform). B-Cyanoethyltrichlorogermanium is converted into B- trichlorogermanium propionic acid (trichlorogermanium propionic acid) by hydrolysis in the presence of a mineral acid and by the action of thionylchloride, this latter compound is converted to trichlorogermanium propionyl chloride. Hydrolysis of this compound with water produces bis-carboxylethyl germanium sesquioxide.
The described-process is illustrated by the following equations:
ChGOCHzCHgCOOH SOC]: Cl GeCH CHgCOOH O=GeCH2CHgCOOH Hydrol sis 2Cl GeCII CHgCOCl -r Bis-carboxyethyl germanium sesquioxide and, so produced, was tested on mice to which Ehrlich ascites tumor has been transplanted.
Test mice: DD Shizuoka, 4 weeks old.
Test procedure:
2,200,000 cells of Ehrlich ascites tumor, as the abnormal cells, were transplanted into the abdomen of mice. After 24 hours, 1 ml. of a sterile aqueous solution of 20 mcg of the compound of the present invention was injected into the abdomens of seven mice and a control into the abdomens of five of the mice. The injection was made every day for 7 days, and on the 8th day, dissection was conducted.
Examining the results, it is seen that the administered group were very vigorous and had good appetite compared with the control group, showing no external appearance of reaction, the control group showed stagnant ascites whereas the administered group showed neither ascites stagnation nor bleeding, the proportion of the number of tumor cells in the bodies of the administered group was approximately 26 percent against percent in the bodies of the control group, and that there was a good indication of the effective checking of fissiparism.
The compound, bis-carboxyethyl germanium sesquioxide is a, are white, crystalline powder, and capable of polymerization on heating. Its melting point is impossible to measure, since heating to a higher temperature causes decomposition. In water solution, the oxygen in germanium sesquioxide is hydrated and the hydrogen stimulates charge transfer, thus causing activation. 7
The novel compound according to the present invention is of a very low order of toxicity. The LD in mice as determined by hypodermic injection is 3,5g/kg of body weight.
The compound of the invention is soluble in water, and therefore it is most convenient to formulate it as solutions in sterile, pyrogen-free water, although any pharmaceutically acceptable carrier may be used.
A preferred therapeutic composition of the invention will comprise an aqueous solution containing from 0.01 to 0.4 by weight of the active ingredient.
Compositions containing the compound according to the invention can be administered orally or Number of E.A.'I. Ascites amount, Aver- '1.I.,
Total age percent Summary TABLE Weight Just be- Third Sixth fore dising day day section ml. Unit Mouse Startnumber X X L are 1 +1.). 1. 1 +L+1+++ i 1111 +0 dfiadfi n n i zuu ..(,.l .(E.( g nnmwdfi 3 0M .123 1 1111 3. .11.). 110%. ++d+ d (.m dd wsdd m M m W+ mi w a w ++H+ eeh++ d md d+ d+ no 2+ H H e 1 e T T n P m d Ham WDH @(G 0.0%WH 11. 1 H .20.. 11111 ++M mmTTmTr +r+r r immim m ++TTT \J A11 A v e s s 1 1 a n 111 001 12 .1 .1111 fiififii fiafia H 11 h 1 1. 1 1 1 0 w EEEEEEE E(E(E W(EE(EE( ((EEE wwwwwww .1. m 1 ..1..1..1..1,.1:1.1. L nmr ur nrnnr 1 1 1 SSSSSSS AA WW m m n 1 1 .SSQ WWWWW V W WW 1.111.111 11 1 1. m m mwfinmw mm mmmm mwmmwmm Mmwmm H 0 S [l 1 P wi ll a m a 1 m m a e m 2 m 1% a a W L 1 W W 2 4 m 3 9 H 1 w M 7 m 7 E 1. d a E W i w m i w a 2 4 e w 4 3 4 0 7. W W 1 2 W M To" m 7 4 00 0 0 V 4 8 1 21 wwww wm wmmmmmw m mm i w w w m 72 6 7 1 1 5 :1. e i i i ii. 1 4528 2 E l 4 25 no" H W W M O m 0m00000 OTW O W 00000 w +w w w 2 0 W 4 W mm%m% 80m5006 9 8722 47 .m 1 .M H .m U WM m 435-WvH6J0 m m m n o i 1 X M m N t 6818722 4877880 0057808 71471 .11 .1 1. w u m .m 11 1 1102100 1 5 0 1 3 m o. w e E u m m H w m m T 5005373 50550? 20520 e m m 11 2100 11121 01 001 2110 L5 0 L3 0 S0 0.0.00.0.00 20551 W m 5 Am 1 11001 ++01+ 1 h m a 1 e .10. W S. 9 7++ I t 12 1 1 :1 v 50 0 S "4 g +1 0 1 r m n Mum 0 505 0 5002545 3355403 551 m 0 23 2 1 w m mwm 1 110 2 +1+ ++&++ ++0 1+ 12 1 2 m m w m m 1 0 0 ++0 0 o 5 0 +o 5 0 5 5 0 ++0 H and .1... w m .5. 30.23 0 1 3 2% 2 1 12 22 0 3 0 S r 2 0Rwflw0m w9 4 m a m 2212111 2% n m 2 m 0 0 90 0 0 5 H r M h 0 3 50126 55 04550 du fl 22121 w o d .1 ma 1 2u122o ++L+++ L21o 1 +d+a 2 2 2 m m m n h s n++ 5 1 0 20 0 ;m0 a 0 +5 0 00500 00655 m M m m 0 010 0 5 ammaminwii 0 5 0 2190.002 0 c 2212122 t W W mmm H 1 m 1 I a 1 0b dv. 0500500 0 05505 0505500 00555 505500 I m lo( ha 1 Lnwowowomomm MMM MN M u mm d flmwwwwfl WEED mm mflmflflmm mmmmwm 221111 mN m e m T 150. N ww m 505 50 5000500 5050505 50550 1234507 23456 5 O LO-9990 22222 W Fr. 221111 9 mmmmwmwm wmw2mmfl N m t n hfl .1 L m 12345 6 89 i ll m mflm mr 67 m REM w flllmm H%M%% m km U0 MW =Ec N lill u il i i Y S v 1 X H e T .T 1 m mm w h H r ix m L MA o m l av n.m r M H m "w ma T 1b] t Bem 0 lmmmw m B C Kdnu A B C 0 One millilitre of physiological salt water.
Example l: To 18 gr. of germaniumchloroform are added 6 gr. of acrylonitrile, and by heating under an atmosphere of 55 nitrogengas, Byanoethyltrichlorogermanium is obtained. This is converted to B-trichlorogermanium propionic acid by adding hydrochloric acid solution and heating. This is converted through reaction upon the dropwise addition of 12 gr. of thionylchloride, to trichlorogermanium propionyl chloride, which is recovered by distillation in vacuo. After complete hydrolysis takes place with water, bis-carboxyethyl germanium sesquioxide is obtained. This is washed with water until chlorine reaction disappears and a white powder is obtained. The yield is about 6 gr. Anal. calcd. for C,l-l ,O,(I1E Calculated value: 1 H2294, Ge:42.64 Found 113.00, Ge:42.41
Notes.-Deg.=Degeneration degree; PSW 1= It has been observed that chemical reaction involving the compounds of the invention occurin the body only The following examples will serve to illustrate the preparation of the compounds of the present invention but are not to be construed as limiting in nature.
parenterally by intramuscular or intravenous injection. Also, if the diseased area is defined by a body cavity, the aqueous solution can be applied directly to the diseased area as by a catheter or irrigation. If administration is to be by the oral route, the carrier can be a solid and in the form of a powder or tablet. The solid carrier can be any of those commonly used in making medicinal formulations.
at the site of abnormal cells, and this is believed to give credence to the theory set forth above.
What is claimed is: i l. Bis-carboxyethyl germanium sesquioxide, of the formula O=GcCllzCllgC0Oll O=( eOH:CII2COOH 2. A process of producing bis-carboxyethyl germanium sesquioxide, comprising reacting germaniumchloroform with acrylonitrile to produce B-
Claims (1)
- 2. A process of producing bis-carboxyethyl germanium sesquioxide, comprising reacting germaniumchloroform with acrylonitrile to produce B-cyanoethyltrichlorogermanium; hydrolyzing B--cyanoethyltrichlorogermanium in the presence of a mineral acid to produce B-trichlorogermanium propionic acid; reacting B-trichlorogermanium propionic acid with thionyl chloride to produce trichlorogermanium propionyl chloride; and hydrolyzing trichlorogermanium propionyl chloride to obtain bis-carboxyethyl germanium sesquioxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008568 | 1968-03-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3689516A true US3689516A (en) | 1972-09-05 |
Family
ID=12017251
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US805370A Expired - Lifetime US3689516A (en) | 1968-03-29 | 1969-03-07 | Bis-carboxyethyl germanium sesquioxide and process for preparing same |
Country Status (7)
Country | Link |
---|---|
US (1) | US3689516A (en) |
BE (1) | BE730615A (en) |
CH (1) | CH521376A (en) |
DE (1) | DE1793288B1 (en) |
FR (1) | FR2005110A1 (en) |
GB (1) | GB1257225A (en) |
NL (1) | NL6904836A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066678A (en) * | 1975-10-23 | 1978-01-03 | Ryuichi Sato | 3-trihydroxygermyl propionic acid and its salts and a process for the production thereof |
US4271084A (en) * | 1978-03-01 | 1981-06-02 | Ryuichi Sato | Germanium-containing organic polymer and the process for the production of the same |
US4361579A (en) * | 1979-09-19 | 1982-11-30 | Yoshitomi Pharmaceutical Industries, Ltd. | Organogermanium compounds |
EP0085513A1 (en) * | 1982-02-01 | 1983-08-10 | Industrial Technology Research Institute | Method for preparing organo germanium propionic acid derivatives |
US4508654A (en) * | 1982-02-01 | 1985-04-02 | Industrial Technology Research Institute | Preparation of bis-carboxy ethyl germanium sesquioxide and its propionic acid derivatives |
DE3514659A1 (en) * | 1984-04-25 | 1985-10-31 | Asai Germanium Research Institute, Tokio/Tokyo | ANTIOXIDANT |
US4579961A (en) * | 1982-08-23 | 1986-04-01 | Norihiro Kakimoto | Organogermanium compounds having both hydrophilicity and lipophilicity and process for producing the same |
US4956272A (en) * | 1987-10-29 | 1990-09-11 | Asai Germanium Research Institute Co., Ltd. | Organogermanium containing solution for washing and storing separated organs |
US5006553A (en) * | 1987-10-29 | 1991-04-09 | Asai Germanium Research Institute Co., Ltd. | Agent for improving reduced functions of organs caused by inhibited blood circulation |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3812167A (en) * | 1971-08-27 | 1974-05-21 | Pahk Heart Foundation | Germanium derivative |
JPS5473129A (en) * | 1977-11-22 | 1979-06-12 | Asai Germanium Res Inst | External skin remedy |
JPS55122717A (en) * | 1979-03-15 | 1980-09-20 | Asai Gerumaniumu Kenkyusho:Kk | Interferon inducer |
JPS6016924A (en) * | 1983-07-11 | 1985-01-28 | Asai Gerumaniumu Kenkyusho:Kk | Antineoplastic agent |
JP2698870B2 (en) * | 1987-10-29 | 1998-01-19 | 株式会社浅井ゲルマニウム研究所 | Agent for reducing nephrotoxicity by administration of cyclosporine |
EP0404062A3 (en) * | 1989-06-20 | 1991-09-25 | Sanwa Kagaku Kenkyusho Co., Ltd. | Organogermanium compound, process for preparation of same as well as use thereof |
-
1968
- 1968-08-27 DE DE19681793288 patent/DE1793288B1/en active Pending
- 1968-10-21 CH CH1569168A patent/CH521376A/en not_active IP Right Cessation
-
1969
- 1969-03-07 US US805370A patent/US3689516A/en not_active Expired - Lifetime
- 1969-03-28 FR FR6909416A patent/FR2005110A1/fr active Pending
- 1969-03-28 BE BE730615D patent/BE730615A/xx not_active IP Right Cessation
- 1969-03-28 NL NL6904836A patent/NL6904836A/xx unknown
- 1969-03-31 GB GB1257225D patent/GB1257225A/en not_active Expired
Non-Patent Citations (1)
Title |
---|
Lesbre et al. Compt. Rend. Vol. 247 (1958) p. 471 474 * |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4066678A (en) * | 1975-10-23 | 1978-01-03 | Ryuichi Sato | 3-trihydroxygermyl propionic acid and its salts and a process for the production thereof |
US4271084A (en) * | 1978-03-01 | 1981-06-02 | Ryuichi Sato | Germanium-containing organic polymer and the process for the production of the same |
US4361579A (en) * | 1979-09-19 | 1982-11-30 | Yoshitomi Pharmaceutical Industries, Ltd. | Organogermanium compounds |
EP0085513A1 (en) * | 1982-02-01 | 1983-08-10 | Industrial Technology Research Institute | Method for preparing organo germanium propionic acid derivatives |
US4420430A (en) * | 1982-02-01 | 1983-12-13 | Industrial Technology Research Institute | Method for preparing organo germanium propionic acid derivatives |
US4508654A (en) * | 1982-02-01 | 1985-04-02 | Industrial Technology Research Institute | Preparation of bis-carboxy ethyl germanium sesquioxide and its propionic acid derivatives |
US4579961A (en) * | 1982-08-23 | 1986-04-01 | Norihiro Kakimoto | Organogermanium compounds having both hydrophilicity and lipophilicity and process for producing the same |
DE3514659A1 (en) * | 1984-04-25 | 1985-10-31 | Asai Germanium Research Institute, Tokio/Tokyo | ANTIOXIDANT |
US4720564A (en) * | 1984-04-25 | 1988-01-19 | Asai Germanium Research Institute | Antioxidant organogermanium compound |
US4956272A (en) * | 1987-10-29 | 1990-09-11 | Asai Germanium Research Institute Co., Ltd. | Organogermanium containing solution for washing and storing separated organs |
US5006553A (en) * | 1987-10-29 | 1991-04-09 | Asai Germanium Research Institute Co., Ltd. | Agent for improving reduced functions of organs caused by inhibited blood circulation |
Also Published As
Publication number | Publication date |
---|---|
BE730615A (en) | 1969-09-01 |
CH521376A (en) | 1972-04-15 |
FR2005110A1 (en) | 1969-12-05 |
NL6904836A (en) | 1969-10-01 |
DE1793288B1 (en) | 1971-05-27 |
GB1257225A (en) | 1971-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3689516A (en) | Bis-carboxyethyl germanium sesquioxide and process for preparing same | |
Storer et al. | Protective effect of para-aminopropiophenone against lethal doses of X-radiation | |
EP0324154A2 (en) | 1,2 Bis(aminomethyl)cyclobutane-platinum-complexes | |
LU83982A1 (en) | PLATIN-DIAMINE COMPLEXES, A METHOD FOR THE PRODUCTION THEREOF, A METHOD FOR THE PRODUCTION OF A MEDICINAL PRODUCT USING SUCH A PLATIN-DIAMINE COMPLEX FOR THIS TREATMENT OF CANCER AND THE ARMY OBTAINED THEREOF | |
EP0552240A1 (en) | New method of treating depression | |
US4892735A (en) | Platinum chemotherapeutic product | |
US2761807A (en) | Glycocyamine and methylating agent in vivo creatine producing composition | |
US2561468A (en) | p-n-mono- and disubstituted aminohydroxyalkylbenzoates and processes of producing same | |
US3988461A (en) | Pharmaceutical composition for the treatment of Parkinson's disease | |
DE3424107A1 (en) | ORGANOGERMANIUM COMPOUND AND THIS ACTIVE INGREDIENT OPIOID PEPTIDAS INHIBITOR | |
US2781291A (en) | Magnesium chelate of ethylenediaminetetraacetic acid for treatment of hypertension | |
US2507468A (en) | Monobasic phosphate of 1-phenyl-2-aminopropane | |
US2939817A (en) | Method of treating diseases associated with plasmin activity | |
DE3011274A1 (en) | SYNERGISTIC RADIATION PROTECTIVE PHARMACEUTICAL PREPARATIONS AND THEIR PRODUCTION | |
US4241084A (en) | Antibacterial and antifungal compositions | |
US3439091A (en) | Method of treatment with modified tetracycline compounds and composition therefor | |
GB1272337A (en) | New basic carbamates and preparation thereof | |
FR2677650B1 (en) | RETINOUIDES SUBSTITUTED BY A DITHIAN CYCLE AND THEIR USE, PROCESS FOR PREPARING THE SAME, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THERAPEUTIC USE THEREOF. | |
US3196076A (en) | Anti-depressant 10-(3-dimethylaminopropyl)-3-azaphenothiazine | |
DE2924077C2 (en) | ||
US3436458A (en) | Antispasmodic and gastric antisecretory compositions containing rho-phenylphenacyl derivatives of 1-hyoscyamine and d,1-tropylatropine | |
CA1155395A (en) | Pharmaceutical composition having normolipidemic and platelet anti-binding activity | |
Hunt | Notes on Acetyl-Methyl-Choline | |
US2851393A (en) | Beta-diethylamino butyric acid anilide, nontoxic salts thereof and aqueous local anesthetic solutions therewith | |
US3655892A (en) | Pharmaceutical preparations and methods of using same |