JPH0351686B2 - - Google Patents

Info

Publication number: JPH0351686B2
Authority: JP; Japan
Prior art keywords: ipriflavone; mitochondria; isoflavone; isopropoxy; pharmaceutical composition
Prior art date: 1977-04-20
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

Application number

JP5110677A

Other languages

English (en)

Japanese (ja)

Other versions

JPS53133635A (en

Inventor

Ratsuzuro Fuyuuru

Miiharii Noguradei

Angesu Gotesugen

Borubara Berumesu

Yanosu Sutererisuzukii

Andorasu Uorufuneru

Rorando Fuarukasu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

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.)

1977-04-20

Filing date

1977-05-02

Publication date

1991-08-07

1977-05-02 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1978-11-21 Publication of JPS53133635A publication Critical patent/JPS53133635A/ja

1991-08-07 Publication of JPH0351686B2 publication Critical patent/JPH0351686B2/ja

Status Granted legal-status Critical Current

Links

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 claims description 36
229960005431 ipriflavone Drugs 0.000 claims description 34
210000003470 mitochondria Anatomy 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 8
230000036284 oxygen consumption Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 7
239000002775 capsule Substances 0.000 claims description 6
102000000587 Glycerolphosphate Dehydrogenase Human genes 0.000 claims description 2
108010041921 Glycerolphosphate Dehydrogenase Proteins 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims 1
210000004072 lung Anatomy 0.000 claims 1
230000000694 effects Effects 0.000 description 22
102000004190 Enzymes Human genes 0.000 description 12
108090000790 Enzymes Proteins 0.000 description 12
239000000203 mixture Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
238000000034 method Methods 0.000 description 9
210000003205 muscle Anatomy 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
230000002438 mitochondrial effect Effects 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
102000018832 Cytochromes Human genes 0.000 description 6
108010052832 Cytochromes Proteins 0.000 description 6
241000700159 Rattus Species 0.000 description 6
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
229920002527 Glycogen Polymers 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
241000283973 Oryctolagus cuniculus Species 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229940096919 glycogen Drugs 0.000 description 5
210000002311 liver mitochondria Anatomy 0.000 description 5
206010002383 Angina Pectoris Diseases 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 4
230000037396 body weight Effects 0.000 description 4
230000007423 decrease Effects 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
235000021317 phosphate Nutrition 0.000 description 4
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 4
239000000758 substrate Substances 0.000 description 4
230000008961 swelling Effects 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
230000001256 tonic effect Effects 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 3
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 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
230000002440 hepatic effect Effects 0.000 description 3
239000008101 lactose Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
239000000902 placebo Substances 0.000 description 3
229940068196 placebo Drugs 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
230000008569 process Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
102000000634 Cytochrome c oxidase subunit IV Human genes 0.000 description 2
108050008072 Cytochrome c oxidase subunit IV Proteins 0.000 description 2
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000002715 bioenergetic effect Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
210000000805 cytoplasm Anatomy 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
210000005228 liver tissue Anatomy 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000011164 ossification Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
210000001685 thyroid gland Anatomy 0.000 description 2
230000032258 transport Effects 0.000 description 2
WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
102000006404 Mitochondrial Proteins Human genes 0.000 description 1
108010058682 Mitochondrial Proteins Proteins 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000006538 anaerobic glycolysis Effects 0.000 description 1
230000003257 anti-anginal effect Effects 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
230000033558 biomineral tissue development Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
238000009585 enzyme analysis Methods 0.000 description 1
238000013401 experimental design Methods 0.000 description 1
210000000720 eyelash Anatomy 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
230000034659 glycolysis Effects 0.000 description 1
230000002414 glycolytic effect Effects 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
210000003494 hepatocyte Anatomy 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
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 1
235000008696 isoflavones Nutrition 0.000 description 1
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
238000011068 loading method Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
-1 manganese-citrate-diethylparaphenylenediamine complexes Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
230000014978 mitochondrial calcium ion transport Effects 0.000 description 1
230000008965 mitochondrial swelling Effects 0.000 description 1
230000004220 muscle function Effects 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 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
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
210000003699 striated muscle Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)

JP5110677A 1977-04-20 1977-05-02 Pharmaceutical composition Granted JPS53133635A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI001729		1977-04-20

Publications (2)

Publication Number	Publication Date
JPS53133635A JPS53133635A (en)	1978-11-21
JPH0351686B2 true JPH0351686B2 (de)	1991-08-07

Family

ID=10994642

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5110677A Granted JPS53133635A (en)	1977-04-20	1977-05-02	Pharmaceutical composition

Country Status (1)

Country	Link
JP (1)	JPS53133635A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE169924T1 (de) *	1993-05-18	1998-09-15	Takeda Chemical Industries Ltd	Benzopyran-derivate und ihre verwendung
JP5384777B2 (ja) *	2001-12-18	2014-01-08	有限会社大長企画	強筋肉剤、抗炎症剤

1977
- 1977-05-02 JP JP5110677A patent/JPS53133635A/ja active Granted

Also Published As

Publication number	Publication date
JPS53133635A (en)	1978-11-21

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