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Medical / Technical Aspect of ORGANICGERMANIUM (US PATENT #04). By -ATP GlobalFoundation. Series -#031

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GERMANIUM (US PATENT #04).By - ATP Global Foundtion.

Series # 031---------------------------------

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R e m e d y f o r b o n e d i s e a s e

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Orimo , et al. April 18, 1989

Remedy for bonedisease

AbstractThis invention provides remedies for bone diseases characterized bycomprising organogermaniumcompounds expressed by the followingformula: ##STR1## (wherein R.sub.1,R.sub.2 and R.sub.3 respectivelydenote a hydrogen atom, a lower alkylgroup such as a methyl or ethyl group,or a substituted or non-substitutedphenyl group; X denotes a hydroxyl, O-lower alkyl or amino group; and Ydenotes an oxygen or sulfur atom) asan effective ingredient. Theseremedies are effect for the remedy of osteoporosis.


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Inventors: Orimo; Hajime (Tokyo, JP); Kakimoto; NorihiroJP); Miyao; Kohei (Tokyo, JP)

Assignee: Asai Germanium Research Institute (Tokyo, JP)Appl. No.: 058278Filed: June 4, 1987

Foreign Application Priority DataJun 18, 1986[JP] 61-142198

Current U.S. Class:

Intern'l Class: A61K 031/32; A61KField of Search: References Cited [Referenced By]

U.S. Patent Documents3812167 May., 1974 Pahk4420430 Dec., 1983 Chang et al.4508654 Apr., 1985 Chang et al.

Foreign Patent Documents55-105696 Aug., 1980 JP57-203090 Dec., 1982 JP203090 Dec., 1982 JP58-146507 Sep., 1983 JP59-184193 Oct., 1984 JP61-145116 Feb., 1986 JP

145116 Jul., 1986 JP1365997 Sep., 1974 GB2158070 Nov., 1985 GB

Primary Examiner: Shaver; Paul F.
http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=/netahtml/search-adv.htm&r=0&f=S&l=50&d=CR89&Query=ref/4,822,817http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/3812167http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/4420430http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/4508654http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=/netahtml/search-adv.htm&r=0&f=S&l=50&d=CR89&Query=ref/4,822,817http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/3812167http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/4420430http://patft.uspto.gov/netacgi/nph-Parser?Sect2=PTO1&Sect2=HITOFF&p=1&u=/netahtml/search-bool.html&r=1&f=G&l=50&d=PALL&RefSrch=yes&Query=PN/4508654


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Attorney, Agent or Firm: Burns, Doane, Swecker & Mathis

ClaimsWe claim:

1. A method for ameliorating the imbalance between osteogenesibone resorption, said method comprising administering to an orgain need of such treatment an effective amount to ameliorate theimbalance between osteogenesis and bone resorption of aof the formula: ##STR6## wherein R.sub.1, R.sub.2 and R.sub.3independently selected from a hydrogen atom, a lower alkyl groupa phenyl group; X denotes a hydroxyl, O-lower alkyl or amino grouand Y denotes an oxygen or sulfur atom.

2. The method as claimed in claim 2 wherein the lower alkyl grou

methyl group, an ethyl group, a propyl group or a butyl group.

3. The method as claimed in claim 1 wherein R.sub.1, R.sub.2 anR.sub.3 are each a hydrogen atom.

4. The method as claimed in claim 1 wherein R.sub.1, R.sub.2 anR.sub.3 is a phenyl group.

5. The method as claimed in claim 1 wherein X is a hydroxyl grou

6. The method as claimed in claim 1 wherein Y is an oxygen atom

7. The method as claimed in claim 6 wherein R.sub.1,


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R.sub.3 are each a hydrogen atom, X is a hydroxyl group and Y isoxygen atom.

8. The method as claimed in claim 1 wherein Y is a sulfur atom.

9. The method as claimed in claim 8 wherein R.sub.1, R.sub.2 anR.sub.3 are each a hydrogen atom, X is a hydroxyl group and Y issulfur atom

Description

BACKGROUND OF THE INVENTION

The present invention relates to remedies for bone diseases, andparticularly to strong remedies for bone diseases containingorganogermanium compounds as effective ingredients.

Recently, metabolic bone diseases such as senile osteoporosis a

renal osteodystrophy, which are due to calcium metabolism or othcauses related thereto, have been increasing. In addition, suchdiseases have become a matter of great concern in the medical fibecause the pathologic physiology of the above-described metabbone diseases and analytical methods concerned therewith whichunknown heretofore have been established.

It is generally said that the above-described bone diserelated to calcium metabolism and abnormalities thereof. For exait is thought that senile osteoporosis is caused by a decrease inosteogenesis compared with bone resorption produced by animbalance between osteogenesis and bone resorption due tocombinations of calcium metabolism and other factors.


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Since this sort of disease however creates pain which is generallydifficult to counteract with usual analgesics or is accompanied witillnesses in which bones easily break and are difficremedy is required.

Since the above-described metabolic bone diseases are, however a single disease but a general term for a particular pathology andcauses have not yet been determined, or various views about theiorigins have been advanced, there are problems with respect to th

difficulty in establishing therapeutics and remedies for such bonediseases.

On the other hand, although calcitonon and active vitamin D haverecently developed as a remedy for metabolic bone diseases, theieffects cannot be said to be strong and they have disadvantages ithey have strong side-effects and are difficult to use.

SUMMARY OF THE INVENTION

The present invention has been achieved against the backgroundthe situation described above, and is characterized by comprisingorganogermanium compounds expressed by the following formula##STR2## (wherein R.sub.1, R.sub.2 and R.sub.3 respectively dea hydrogen atom, a lower alkyl group such as a methyl or ethyl gr

or a substituted or non-substituted phenyl group; X denotes a hydO-lower alkyl or amino group; and Y denotes an oxygen or sulfur as an effective ingredient.

In other words, the inventors have investigated in detail the pathol


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and the origins of the above metabolic bone diseases, have noticorganogermanium compounds and have thought of an effectivetherapeutic for such diseases, utilizing these compounds for thepurpose of, for example, ameliorating the imbalance betweenosteogenesis and bone resorption. Therefore, the inventors haveenergetically researched into usable compounds, resulting in theachievement of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

Germanium (Ge), which is a known metal, is conventionally an objof investigation in the fields of physics and inorganic chemistry.Investigations into organic compounds of germanium have recentlproceeded and the results of these investigations have been activreported, and consequently these organic compounds have attracattention in various technical fields.

For example, it is becoming well known in the field of pharmaceutithat carboxyethylgermanium sesquioxide (GeCH.sub.2 CH.sub.2COOH).sub.2 O.sub.3, which is an organogermanium compoundin which propionic acid derivatives of germanium and oxygen atoare bonded in a ratio of 2:3, exhibits the effects of reducing bloodpressure and amiloyd degeneration, produces excellent physiologreactions such as the activation of macrophages and has an antiteffect obtained by inducing interferons, but exhibits no toxicity and

effects at all, and this compound is being clinically tested.Since the remedies for bone diseases of the present invention cothe organogermanium compounds shown in the above Formeffective ingredients, these compounds are first described below.


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basic skeletons of these compounds are germyl propionic acid inpropionic acid derivatives having three substituents R.sub.1 to R.sand oxygen functional groups OX in molecules are bonded togermanium atoms. The germanium atoms in these basic skeletonbonded to oxygen atoms (when Y=O) or sulfur atoms (when Y=S)the ratio of 2:3.

In these compounds, the substituents R.sub.1, R.sub.2 and R.subrespectively denote a hydrogen atom, a lower alkyl group such asmethyl, ethyl, propyl or butyl group, or a substituted or non-substit

phenyl group; and the substituent X denotes a hydroxyl, O-lower or amino group.

In addition, the substituents R.sub.1 and R.sub.2 are bonded at th.alpha.-position relative to the germanium atom and the substitueR.sub.3 is bonded at the .beta.-position relative to the same. Ther examples of organogermanium compounds used as remedies of tpresent invention include the following compounds: ##STR3##

The organogermanium compounds having the above-describedstructures can be produced by various methods.

For example, when X=OH and Y=O in the above-described formultrihalogermyl propionic acid such as trichlorogermyin which the substituents R.sub.1 to R.sub.3 have been previously

introduced may be hydrolyzed, as shown in the following reactionformula 1: ##STR4##

When X=OH and Y=S in the above formula I, a trihalogermyl propacid such as the above trichlorogermyl propionic acid (1) may be


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reacted with hydrogen sulfide H.sub.2 S, as shown in the followinreaction formula 2: ##STR5##

On the other hand, when X=O-lower alkyl group in the formula I, f example, the above-described compound (1) may be reacted withthionyl chloride to be changed into the corresponding acid halidemay then be reacted with the alcohol corresponding to the above lalkyl group and subsequently with hydrogen sulfide, and which mthen be reacted with ammonia and subsequently with hydrogen swhen X=NH.sub.2 in the formula I.

The results of the instrumental analyses such as the nuclear magresonance (NMR) and the infrared absorption (IR) spectra of theorganogermanium compounds obtained in the abovmethods support well the fact that these compounds are thoseexpressed by the formula I. Remedies for bone diseases of the pr invention contain organogermanium compounds synthesized by tabove-mentioned methods as effective ingredients.experienced in their administration in either oral or parenteral formin the case of oral administration it is possible to utilize conventionused forms such as tablets, capsules, powder or granules.

EFFECT AND FUNCTION OF THE INVENTION

Osteoblasts which are important for bone diseases are cells arran

to form a monolayer cylinder on the surface of osteogenesis andsaid to synthesize organic substrates such as collagen andglycoproteins and to form substrate vesicles so as to deposit bonesuch as hydroxyapatite therein. When the remedies of the presentinvention were allowed to act on these osteoblasts, the effect of di


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activation was recognized.

In addition, since the concentration of the compounds requiredabove-described effect to be exhibited is extremely low, combinedthe low toxicity of the organogermanium compounds per se, it cansaid that the remedies of the present invention are strong and saf The remedies can therefore ameliorate the imbalance betweenosteogenesis and bone resorption and be used for remedyingosteoporosis.

When the remedies of the present invention were actually administo patients with osteoporosis and their effect on bone metabolisminvestigated by measuring the bone-salt content of left radius, asignificant difference was observed between the test group and acontrol group and it was confirmed that the remedies of the preseinvention were effective for the remedy of osteoporosis.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graph showing the feature of activation of clonedosteoblasts by remedies of the present invention;

FIG. 2 is a graph showing the feature of dose response of remedithe prsent invention;

FIG. 3 is a graph showing that remedies of the present invention cprevent the reduction of the bone-salt content of the left radius;

FIG. 4 is a graph showing that remedies of the present invention creduce A1-Pase in blood; and


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FIG. 5 is a graph showing that remedies of the present ireduce iPTH in blood.

DESCRIPTION OF EXAMPLES

The present invention is described in detail below with reference tExperimental Examples and Examples.

EXPERIMENTAL EXAMPLE 1

Synthesis 1 of Organogermanium Compound

500 ml of water was added to 50.4 g (0.2 mol) of trichlorogermylpropionic acid and the mixture was agitated for 1 hour and then allto stand for 24 hours. The separated crystals were filtered andrecrystallized from water to obtain 28.0 g of Compound I1. The valof the physical properties of Compound I1 obrtained correspondethe values reported in literature.

The other compounds were produced in accordance with the metdescribed, for example, in Japanese Patent Laid-Open No.226592/1985.

EXPERIMENTAL EXAMPLE 2

synthesis 2 of Organogermanium Compound

25.2 g (0.1 mol) of trichlorogermyl propionic acid was dissolved inml of anhydrous benzene and 2.4 g (0.1 mol) of anhydrous pyridin


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was added to the resulting solution. The mixture obtained was agiand a dried hydrogen sulfide gas was passed therethrough for 60minutes. Benzene was removed from the mixture with attention bpaid to the oil substance produced which was then dissolved inmethanol. 300 ml of purified water was added to the solution obtaiand the separated crystals were recrystallized from methanol to o17.1 g of Compound I10. The values of the physical properties of Compound I10 obtained corresponded with the values reported inliterature.

The other compounds were produced in accordance with the metdescribed, for example, in Japanese Patent Laid-Open No.35916/1984.

EXAMPLE 1

Examination 1 of Pharmaceutical Effect (Method)

Clone MC3T3-E1 cells obtained from new born mouse calvaria wused as cultivation osteoblasts. The osteoblasts were sown in .alpMEM containing 10% fetal calf serum so as to become 10.sup.5 /and cultivated under the conditions of 37.degree. C. and 95% air/CO.sub.2 until they reached a confluent state.

The effects of remedies of the present invention were examined b

adding the remedies respectively containing as an effective ingredCompounds I1 to I18 into .alpha.-MEM containing 0.3% BSA so ththe final concentration of these compounds became 10 .mu.g/ml.

Alkaline phosphatase was used as an index of the activation of


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osteoblasts and measured after cultivation for 1 to 4 days.

(Result)

By adding the remedies of the present invention, as shown in FIG.the alkaline phosphatase activity of MC3T3-E1 reached a peak aftcultivation for 4 days when Compound I1 was used as a mainingredient (Agent 1 of this invention), and it reached a peak after cultivation for 1 day when Compound I10 was used as a mainingredient (Agent 10 of this invention), with a significant difference

being recognized between the respective agents and a control sa

It was confirmed from the above-described facts that the remediethe present invention were able to increase the activity of clonedosteoblasts. In addition, when the remedies of the present inventicontaining the other compounds as effective ingredients were useresults obtained were substantially the same as those described a

Since the alkaline phosphatase activity reached a peak after culivfor 4 days and 1 day in the cases of Agents 1 and 10 of this invenrespectively, the investigation of the dose response of each caseclarified that Agents 1 and 10 of this invention exhibited the requir effect at concentrations of as low as 100 ng/ml and 10 .mu.g/ml,respectively, as shown in FIG. 2.

EXAMPLE 2Examination 2 of Pharmaceutical Effect

Six capsules of the agent of this invention containing 250 mg of


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Compound I1 as a main ingredient were administered to eight patisuffering from osteoporosis (all patients being female;years old.+-.4 years) for 12 months and the bone-salt content of tradius of each patient was measured before administration starteafter 3, 6, 9 and 12 months had passed.

As seen from FIG. 3, the results obtained clarified thacontent of the left radius in a group to which no agent was adminigradually reduced during the time of observation over the period omonths, while the reduction of the content in a group to which the

of this invention was administered was significantly inhibited.

A significant difference of P 0.05 was found at each of themeasurements after 3, 6 and 12 months.

In addition, it was found that A1-Pase in blood and iPTH in bloodsignificantly reduced, as shown in FIGS. 4 and 5, respectively.

A significant difference of P


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