AU7236694A - Pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereof - Google Patents
Pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereofInfo
- Publication number
- AU7236694A AU7236694A AU72366/94A AU7236694A AU7236694A AU 7236694 A AU7236694 A AU 7236694A AU 72366/94 A AU72366/94 A AU 72366/94A AU 7236694 A AU7236694 A AU 7236694A AU 7236694 A AU7236694 A AU 7236694A
- Authority
- AU
- Australia
- Prior art keywords
- hydrogen
- general formula
- stands
- osteoporosis
- stand
- 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.)
- Abandoned
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title description 7
- 229930012930 isoflavone derivative Natural products 0.000 title description 5
- 150000002515 isoflavone derivatives Chemical class 0.000 title description 5
- 239000013543 active substance Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 10
- 208000001132 Osteoporosis Diseases 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- -1 C gcarbalkoxy Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 2
- 239000012752 auxiliary agent Substances 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 description 6
- SFBODOKJTYAUCM-UHFFFAOYSA-N Ipriflavone Chemical compound C=1C(OC(C)C)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 SFBODOKJTYAUCM-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229960005431 ipriflavone Drugs 0.000 description 5
- 210000002449 bone cell Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 3
- 235000008696 isoflavones Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000033558 biomineral tissue development Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 210000000537 nasal bone Anatomy 0.000 description 2
- 210000002997 osteoclast Anatomy 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 102000004067 Osteocalcin Human genes 0.000 description 1
- 108090000573 Osteocalcin Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000018678 bone mineralization Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002250 eicosanoid group Chemical group 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- BBBFJLBPOGFECG-UHFFFAOYSA-N salmon calcitonin Chemical compound C=1N=CNC=1CC(C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCC(N)=O)C(=O)NC(C(C)O)C(=O)NC(CC=1C=CC(O)=CC=1)C(=O)N1C(CCC1)C(=O)NC(CCCNC(N)=N)C(=O)NC(C(C)O)C(=O)NC(CC(N)=O)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CO)C(=O)NCC(=O)NC(C(C)O)C(=O)N1C(CCC1)C(N)=O)NC(=O)C(CC(C)C)NC(=O)C(CCC(O)=O)NC(=O)C(CCC(N)=O)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C1CSSCC(N)C(=O)NC(CO)C(=O)NC(CC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)N1 BBBFJLBPOGFECG-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
PHARMACEUTICAL COMPOSITIONS CONTAINING AS ACTIVE AGENT ISOFLAVONE DERIVATIVES OR SALTS THEREOF
The present invention relates to pharmaceutical compositions containing as active agent isoflavone derivatives of the general formula
wherein
R1 represents a C2„i8alkyl optionally substituted by Cμgalkoxy, hydroxyl, Cμβcarbalkoxy, phenyl, benzoyl or a halo atom; phenylalkyl containing a C1-_ alkyl chain optionally substituted by a halo atom or a nitro group or C2.6alkenyl; R2 and R3 stand for hydrogen or C^alkoxy; R4 stands for hydrogen, C^aUcyl or carboxyl; R5 stands for hydrogen or C^alkyl; R6 stands for hydrogen or, if R5 stands for hydrogen, R6 may also stand for methyl or hydroxymethyl, with the proviso that if R2, R3, R4, R5 and R6 stand for hydrogen, R1 is other than isopropyl, or salt thereof. The composition can be prepared by admixing an isoflavone derivative of the general formula (I), wherein R1, R2, R3, R4 and R5 are as defined above, prepared in a known manner, with filling, diluting and other auxiliary substances generally used in the pharmaceutical industry and formulating pharmaceutical compositions. The compositions are suitable for the treatment of osteoporosis.
The compounds of the general formula (I) containing a hydrogen atom in the place ofR6 are prepared by a) reacting ketones of the general formula
(III) ,
wherein R5, R1, R2 and R3 are as defined above, with alkyl orthoformiate in the presence of a basic catalyst, or b) reacting ketones of the general formula
wherein R5, R1, R2 and R3 as defined above, with hydrogen cyanide and/or cyanic salts in the presence of a hydrohalogenic acid, or c) reacting ketones of the general formula (HI), wherein R5, R1, R2 and R3 as defined above, with alkyl formiate in the presence of an alkali metal, or d) reacting ketones of the general formula (El), wherein R5, R1, R2 and R3 as defined above, with alkyloxalkyl halide and, if desired, saponifying and/or decarboxylating the isoflavone ester thus obtained, or e) reacting ketones of the general formula (IH), wherein R5, R1, R2 and R3 as defined above, with organic carboxylic acid anhydride, or f) reacting ketones of the general formula (III), wherein R5, R1, R2 and R3 as defined above, with N,N-dialkyl acid amide in the presence of phosporous chloride, or g) dehydrating 2-hydroxy isoflavone derivatives of the general formula
wherein R5, R1, R2 and R3 as defined above, and optionally introducing into a compound of the general formula (I), wherein R1 is hydrogen, an R1 group other than hydrogen, if desired, converting an another R1 group into another R1 group and, if desired, converting a compound of the general formula (I) thus obtained into its salt or setting it free from its salt. (Hungarian Patent Specification No. 162,377)
compounds of the general formula (I) containing a hydrogen atom in position 6 by halomethylation. The reduction is preferably carried out in the presence of metals, preferably zinc.
The compounds of the general formula (I) containing an alkoxy or hydroxymethyl group in position 6 are prepared either by replacing the halo atom of the halometfayl isoflavones prepares as described above by an alkoxy group by the aid of alcohols or by replacing said halo atom by an 0-acetyl group by the aid of sodium acetate and by subsequently converting the acetoxy group into a hydroxy group.
The active agents of the compositions according to the invention can be prepared in a known manner. The term "known manner" comprises all the methods which could be learned from the literature until the date of priority.
According to the Hungarian Patent Specification No. 162,377 the compounds of the general formula (I) and salts thereof exert a cholesterol level decreasing effect in the blood and they influence the metabolism, thus, the majority of these compounds show an anabolitic, while the others show a catabolitic effect.
It is known that osteoporosis is a disease which manifests itself frequently with women being in the menopause.
Oestrogenic preparations, calcitonine, vitamin D and other calcium-containing preparations are used for the treatment of osteoporosis. However, none of these preparations proved to be sufficiently effective against this disease.
We have found that the compounds of the general formula (I) and salts thereof can effectively be used for the prophylaxis and treatment of osteoporosis.
It is known that Ipriflavone (7-Isopropoxy-isofiavone) is able to inhibit bone resoiption either in vitro or in vivo (Notoya, K. et al. Inhibitory effect of
Ipriflavone on pit formation in mouse unfractionated bone cells, Calcif. Tissue Int. 51, (Supl. 1) 53-56 (1992); Notoya, K. et al. Inhibitory effect of Ipriflavone on osteoclast-mediated bone resorption and new osteoclast formation in long-term cultures of mouse unfractionated bone cells, Calcif Tissue Int. 50, 314-319 (1992). On the other hand, it is known that Ipriflavone also could increase the mineralization of the extracellular matrix of human bone cell cultures (Ref. Ecsedi, G.G. Model for in vitro investigation of bone mineralization, Agents and Actions 41, 84-85 (1994.)
To estimate the effectiveness of the compoimds of the general Formula (I) on bone formation an in vitro mineralization model was developed. Under certain circumstances cultures of partially selected (osteoblast-enriched) human bone cells originated from either nasal bone of adults or foetus femur produce Type I collagene, bone specific proteins (e.g. osteocalcin), prostanoides (PGE2, PGF2α, PGI2, etc. and accumulate calcium into the synthesized matrix (Ref: Ecsedi, G.G., Characterization of cells of human nasal bone cell cultures, 4th Int. Symposium on Osteoporosis, 27 March- 2 April, 1993 Hong Kong; Abstr. no. 534). Method, Cells of subcultures 8-12 (usually 8th or 9th) were drop-inoculated at a density of 2* 10Λ4 cells per well 96-well plates. On the day 3 the treatments were started with the compound of the Formula I at two concentrations, 10Λ-8 and 10Λ-10 M. Because ethanolic 10Λ-5 and 10Λ-7 M stock solutions of the compounds were used in the treatments all culture media contained 0J % ethanol including the Controls. Media were changed on each 2-3 day. The treatments were finished on the day 21, the total calcium (Ca) and DNA content of the 6-parallel samples were measured by Boehringer Test Combination (MPR3) and the spectrofluorometric 3,5-diaminobenzoic acid (DABA) method, respectively, then the ratios, Ca/DNA were calculated.
In the table of the compounds of Formula I below, data are given in percentages compared to the average of the Control value (100%)
Name of Concentration Ca DNA Ca/DNA
Compound [-log M] % % %
Ipriflavone 8 121 100 121
(7-isopropoxy- 10 111 108 103 isoflavone)
CH- 16693 8 143 109 131
(7-n-nonyloxy- 10 108 103 104
-isoflavone) covered by the general Formula (I)
CH-2793 8 116 103 113
(7-n-propoxy- 10 180 106 168
-isoflavone) covered by the general Formula (I)
In the treatment the compounds of the general formula (I) can preferably be used in the form of capsules, tablets or tablets with prolonged effect. These pharmaceutical preparation can be made by methods known per se.
The invention is elucidated in detail by the following non-limiting examples. The following compositions are prepared in a known manner:
Example 1 Capsules A compound of the general formula (I) 200 mg colloidal silicic acid 20 mg talc 20 mg magnesium stearate 20 mg lactose 80 mg
Example 2 Tablets
A compound of the general formula (I) 200 mg magnesium stearate 4 mg talc 7 mg polyvinyl-pyrrolidone 13 mg lactose 60 mg potato starch 36 mg Esmaspreny (formaldehyde caseine) 60 mg
Claims (3)
1. A pharmaceutical composition for the treatment of osteoporosis, which comprises as active ingredient a therapeutically active amount of a compound of the general
wherein
R1 represents a C2_18alkyl optionally substituted by C galkoxy, hydroxyl,
C gcarbalkoxy, phenyl, benzoyl or a halo atom; phenylalkyl containing a C^alkyl chain optionally substituted by a halo atom or a nitro group or C2_6alkenyl; R2 and R3 stand for hydrogen or C^alkoxy; R4 stands for hydrogen, C galkyl or carboxyl; R5 stands for hydrogen or C^alkyl; R6 stands for hydrogen or, if R5 stands for hydrogen, R6 may also stand for methyl or hydroxymethyl, with the proviso that if R2, R3, R4, R5 and R6 stand for hydrogen, R1 is other than isopropyl, in admixture with suitable inert, solid or liquid carriers and optionally with usual therapeutical additives and auxiliary agent.
2. Use of compounds of the general formula (I), wherein R1, R2, R3, R4 and R5 are as defined in claim 1, for formulating pharmaceutical compositions for the treatment of osteoporosis.
3. Method of treatment of osteoporosis of an affected human or animal subject, which comprises the step of administering in an effective amount a compound of the general formula (I), wherein R1, R2, R3, R4 and R5 are as defined in claim 1, in admixture with suitable inert, solid or liquid carriers and optionally with usual therapeutical additives and auxiliary agent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2082/93 | 1993-07-20 | ||
| HU9302082A HUT68396A (en) | 1993-07-20 | 1993-07-20 | Method for preparing pharmaceutical preparation containing isoflavone derivative or salt of it |
| PCT/HU1994/000027 WO1995003040A1 (en) | 1993-07-20 | 1994-07-18 | Pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU7236694A true AU7236694A (en) | 1995-02-20 |
Family
ID=10983802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72366/94A Abandoned AU7236694A (en) | 1993-07-20 | 1994-07-18 | Pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereof |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0717621A1 (en) |
| KR (1) | KR960703600A (en) |
| CN (1) | CN1129398A (en) |
| AU (1) | AU7236694A (en) |
| HU (1) | HUT68396A (en) |
| WO (1) | WO1995003040A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1289154B1 (en) * | 1997-01-03 | 1998-09-29 | Chiesi Farma Spa | ISOFLAVONE DERIVATIVES THEIR PREPARATION AND THEIR THERAPEUTIC USE |
| KR100436220B1 (en) * | 2001-08-30 | 2004-06-12 | 주식회사 네패스 | Organic polymers for bottom antireflective coating, processes for preparing the same, and compositions containing the same |
| WO2007099432A2 (en) | 2006-02-28 | 2007-09-07 | Council Of Scientific And Industrial Research | Pharmaceutical composition containing butea isoflavones for the prevention /treatment of bone disorders and a process for the preparation thereof |
| CN101331913B (en) * | 2008-07-22 | 2011-03-16 | 广东新南都饲料科技有限公司 | Use of isoflavone with substituent at intermedium ring 2 position as animal feed additives |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE586723A (en) * | 1960-01-19 | 1960-07-19 | Sarec S A | New chemical and therapeutic compounds derived from isoflavones, and their preparation processes. |
| FR846M (en) * | 1960-01-19 | 1961-10-02 | ||
| HU162377B (en) * | 1970-05-27 | 1973-02-28 | ||
| US3949085A (en) * | 1970-05-27 | 1976-04-06 | Chinoin Gyogyszer-Es Vegyeszeti Termakek Gyara Rt | Anabolic-weight-gain promoting compositions containing isoflavone derivatives and method using same |
| US3864362A (en) * | 1970-05-27 | 1975-02-04 | Chinoin Gyogyszer Es Vegyeszet | Iso flavones |
| US4166862A (en) * | 1971-05-25 | 1979-09-04 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Animal feed containing anabolic isoflavones |
| AT339130B (en) * | 1971-10-20 | 1977-10-10 | Chinoin Gyogyszer Es Vegyeszet | WEIGHT INCREASING FEED ADDITIVE |
| HU166380B (en) * | 1973-07-09 | 1975-03-28 | ||
| JPS60132917A (en) * | 1983-12-21 | 1985-07-16 | Takeda Chem Ind Ltd | Remedy for osteoporosis |
-
1993
- 1993-07-20 HU HU9302082A patent/HUT68396A/en unknown
-
1994
- 1994-07-18 KR KR1019960700363A patent/KR960703600A/en not_active Application Discontinuation
- 1994-07-18 EP EP94921775A patent/EP0717621A1/en not_active Withdrawn
- 1994-07-18 WO PCT/HU1994/000027 patent/WO1995003040A1/en not_active Application Discontinuation
- 1994-07-18 CN CN94193116A patent/CN1129398A/en active Pending
- 1994-07-18 AU AU72366/94A patent/AU7236694A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| HUT68396A (en) | 1995-04-25 |
| EP0717621A1 (en) | 1996-06-26 |
| CN1129398A (en) | 1996-08-21 |
| HU9302082D0 (en) | 1993-10-28 |
| WO1995003040A1 (en) | 1995-02-02 |
| KR960703600A (en) | 1996-08-31 |
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