WO1995003040A1 - Compositions pharmaceutiques contenant comme agent actif des derives de'isoflavone ou des sels de ceux-ci - Google Patents

Compositions pharmaceutiques contenant comme agent actif des derives de'isoflavone ou des sels de ceux-ci Download PDF

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Publication number
WO1995003040A1
WO1995003040A1 PCT/HU1994/000027 HU9400027W WO9503040A1 WO 1995003040 A1 WO1995003040 A1 WO 1995003040A1 HU 9400027 W HU9400027 W HU 9400027W WO 9503040 A1 WO9503040 A1 WO 9503040A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen
stands
general formula
stand
alkyl
Prior art date
Application number
PCT/HU1994/000027
Other languages
English (en)
Inventor
Mihály NÓGRÁDI
Ágnes GOTTSEGEN
Sándor ANTUS
János STRELISKY
Borbála VERMES
András WOLFNER
Ádám MAJOR
Tamás Szüts
Istvánné BENDEFFY
Tamásné Mármarosi
Original Assignee
Chinoin Ltd.
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.)
Filing date
Publication date
Application filed by Chinoin Ltd. filed Critical Chinoin Ltd.
Priority to KR1019960700363A priority Critical patent/KR960703600A/ko
Priority to EP94921775A priority patent/EP0717621A1/fr
Priority to AU72366/94A priority patent/AU7236694A/en
Publication of WO1995003040A1 publication Critical patent/WO1995003040A1/fr

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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

Definitions

  • the present invention relates to pharmaceutical compositions containing as active agent isoflavone derivatives of the general formula
  • R 1 represents a C 2 personallyi 8 alkyl optionally substituted by C ⁇ galkoxy, hydroxyl, C ⁇ carbalkoxy, phenyl, benzoyl or a halo atom; phenylalkyl containing a C 1 -_ alkyl chain optionally substituted by a halo atom or a nitro group or C 2 .
  • R 2 and R 3 stand for hydrogen or C ⁇ alkoxy
  • R 4 stands for hydrogen, C ⁇ aUcyl or carboxyl
  • R 5 stands for hydrogen or C ⁇ alkyl
  • R 6 stands for hydrogen or, if R 5 stands for hydrogen, R 6 may also stand for methyl or hydroxymethyl, with the proviso that if R 2 , R 3 , R 4 , R 5 and R 6 stand for hydrogen, R 1 is other than isopropyl, or salt thereof.
  • the composition can be prepared by admixing an isoflavone derivative of the general formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 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 ofR 6 are prepared by a) reacting ketones of the general formula
  • R 5 , R 1 , R 2 and R 3 are as defined above, with alkyl orthoformiate in the presence of a basic catalyst, or b) reacting ketones of the general formula
  • R 5 , R 1 , R 2 and R 3 as defined above, and optionally introducing into a compound of the general formula (I), wherein R 1 is hydrogen, an R 1 group other than hydrogen, if desired, converting an another R 1 group into another R 1 group and, if desired, converting a compound of the general formula (I) thus obtained into its salt or setting it free from its salt.
  • R 1 is hydrogen, an R 1 group other than hydrogen
  • converting an another R 1 group into another R 1 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.
  • 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.
  • 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.
  • 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).
  • Ipriflavone also could increase the mineralization of the extracellular matrix of human bone cell cultures (Ref. Ecsedi, G.G.
  • 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.
  • 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
  • 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

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  • 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)

Abstract

La présente invention se rapporte à des compositions pharmaceutiques contenant comme agent actif des dérivés de l'isoflavone de la formule générale (I), dans laquelle R1 représente un groupe alkyle C¿2-18? éventuellement substitué par alcoxyC1-6, hydroxyle, carbalcoxyC1-6, phényle, benzoyle ou un atome halo; phénylalkyle contenant une chaîne alkyle C1-3 éventuellement substituée par un atome halo ou un groupe nitro ou alcényleC2-6; R?2 et R3¿ remplacent hydrogène ou alcoxyC¿1-6; R?4 remplace hydrogène, alkyleC¿1-6? ou carboxyle; R?5¿ remplace hydrogène ou alkyleC¿1-4; R?6 remplace hydrogène ou, si R5 remplace hydrogène, R6 peut également remplacer méthyle ou hydroxyméthyle, à condition que, si R?2, R3, R4, R5 et R6¿ remplacent hydrogène, R1 soit différent d'isopropyle, ou un sel de celui-ci. Les compositions pharmaceutiques de l'invention sont préparées à l'aide de procédés connus et sont appropriées au traitement de l'ostéoporose.
PCT/HU1994/000027 1993-07-20 1994-07-18 Compositions pharmaceutiques contenant comme agent actif des derives de'isoflavone ou des sels de ceux-ci WO1995003040A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1019960700363A KR960703600A (ko) 1993-07-20 1994-07-18 활성제로서 이소플라본 유도체 또는 그것의 염을 포함하는 제약학적인 조성물(pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereof)
EP94921775A EP0717621A1 (fr) 1993-07-20 1994-07-18 Compositions pharmaceutiques contenant comme agent actif des derives de'isoflavone ou des sels de ceux-ci
AU72366/94A AU7236694A (en) 1993-07-20 1994-07-18 Pharmaceutical compositions containing as active agent isoflavone derivatives or salts thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU9302082A HUT68396A (en) 1993-07-20 1993-07-20 Method for preparing pharmaceutical preparation containing isoflavone derivative or salt of it
HU2082/93 1993-07-20

Publications (1)

Publication Number Publication Date
WO1995003040A1 true WO1995003040A1 (fr) 1995-02-02

Family

ID=10983802

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU1994/000027 WO1995003040A1 (fr) 1993-07-20 1994-07-18 Compositions pharmaceutiques contenant comme agent actif des derives de'isoflavone ou des sels de ceux-ci

Country Status (6)

Country Link
EP (1) EP0717621A1 (fr)
KR (1) KR960703600A (fr)
CN (1) CN1129398A (fr)
AU (1) AU7236694A (fr)
HU (1) HUT68396A (fr)
WO (1) WO1995003040A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998029403A1 (fr) * 1997-01-03 1998-07-09 Chiesi Farmaceutici S.P.A. Derives de l'isoflavone, procedes pour les preparer et compositions pharmaceutiques les contenant__________________________________________________________________________________________________
KR100436220B1 (ko) * 2001-08-30 2004-06-12 주식회사 네패스 바닥 반사방지막용 유기 중합체, 그의 제조방법 및 그를함유하는 조성물
WO2007099432A2 (fr) 2006-02-28 2007-09-07 Council Of Scientific And Industrial Research composition pharmaceutique pour la prévention/le traitement de troubles osseux et son processus d'élaboration

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101331913B (zh) * 2008-07-22 2011-03-16 广东新南都饲料科技有限公司 一类中间环2位带有取代基的异黄酮作为动物饲料添加剂的应用

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR846M (fr) * 1960-01-19 1961-10-02
US3352754A (en) * 1960-01-19 1967-11-14 Sarec S A Therapeutic compositions comprising isoflavone compounds
DE2166458A1 (de) * 1970-05-27 1974-10-03 Chinoin Gyogyszer Es Vegyeszet Metabolisch wirkendes mittel
US3864362A (en) * 1970-05-27 1975-02-04 Chinoin Gyogyszer Es Vegyeszet Iso flavones
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
AT339130B (de) * 1971-10-20 1977-10-10 Chinoin Gyogyszer Es Vegyeszet Gewichtssteigernder futtermittelzusatz
US4163746A (en) * 1973-07-09 1979-08-07 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Metabolic 5-methyl-isoflavone-derivatives, process for the preparation thereof and compositions containing the same
US4166862A (en) * 1971-05-25 1979-09-04 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Animal feed containing anabolic isoflavones
DE3446246A1 (de) * 1983-12-21 1985-07-11 Takeda Chemical Industries, Ltd., Osaka Verwendung von 3-phenyl-4h-1-benzopyran-4-on-derivaten zur verhuetung und behandlung von osteoporose

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR846M (fr) * 1960-01-19 1961-10-02
US3352754A (en) * 1960-01-19 1967-11-14 Sarec S A Therapeutic compositions comprising isoflavone compounds
DE2166458A1 (de) * 1970-05-27 1974-10-03 Chinoin Gyogyszer Es Vegyeszet Metabolisch wirkendes mittel
US3864362A (en) * 1970-05-27 1975-02-04 Chinoin Gyogyszer Es Vegyeszet Iso flavones
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
US4166862A (en) * 1971-05-25 1979-09-04 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Animal feed containing anabolic isoflavones
AT339130B (de) * 1971-10-20 1977-10-10 Chinoin Gyogyszer Es Vegyeszet Gewichtssteigernder futtermittelzusatz
US4163746A (en) * 1973-07-09 1979-08-07 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Metabolic 5-methyl-isoflavone-derivatives, process for the preparation thereof and compositions containing the same
DE3446246A1 (de) * 1983-12-21 1985-07-11 Takeda Chemical Industries, Ltd., Osaka Verwendung von 3-phenyl-4h-1-benzopyran-4-on-derivaten zur verhuetung und behandlung von osteoporose

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Soviet Inventions Illustrated, Section CH, week C 15, 21 May 1980 (21.05.80), Derwent Publications LTD London, B 02; & SU,A,682 099 (CHINOIN GYOGYSZER). *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998029403A1 (fr) * 1997-01-03 1998-07-09 Chiesi Farmaceutici S.P.A. Derives de l'isoflavone, procedes pour les preparer et compositions pharmaceutiques les contenant__________________________________________________________________________________________________
KR100436220B1 (ko) * 2001-08-30 2004-06-12 주식회사 네패스 바닥 반사방지막용 유기 중합체, 그의 제조방법 및 그를함유하는 조성물
WO2007099432A2 (fr) 2006-02-28 2007-09-07 Council Of Scientific And Industrial Research composition pharmaceutique pour la prévention/le traitement de troubles osseux et son processus d'élaboration
WO2007099432A3 (fr) * 2006-02-28 2007-11-22 Council Scient Ind Res composition pharmaceutique pour la prévention/le traitement de troubles osseux et son processus d'élaboration
JP2009536610A (ja) * 2006-02-28 2009-10-15 カウンシル オブ サイエンティフィク アンド インダストリアル リサーチ 骨疾患の予防／治療のための医薬組成物及びその調製方法

Also Published As

Publication number Publication date
EP0717621A1 (fr) 1996-06-26
HU9302082D0 (en) 1993-10-28
AU7236694A (en) 1995-02-20
HUT68396A (en) 1995-04-25
KR960703600A (ko) 1996-08-31
CN1129398A (zh) 1996-08-21

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