JPS5925599B2 - 新生理活性物質モナコリンｋおよびその製造法 - Google Patents
新生理活性物質モナコリンｋおよびその製造法Info
- Publication number
- JPS5925599B2 JPS5925599B2 JP54017856A JP1785679A JPS5925599B2 JP S5925599 B2 JPS5925599 B2 JP S5925599B2 JP 54017856 A JP54017856 A JP 54017856A JP 1785679 A JP1785679 A JP 1785679A JP S5925599 B2 JPS5925599 B2 JP S5925599B2
- Authority
- JP
- Japan
- Prior art keywords
- monacolin
- monascus
- substance
- methanol
- active substance
- 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
Links
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 title claims description 38
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000013543 active substance Substances 0.000 title claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 241000228347 Monascus <ascomycete fungus> Species 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- 241000894006 Bacteria Species 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000012258 culturing Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000862 absorption spectrum Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004809 thin layer chromatography Methods 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 238000004949 mass spectrometry Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 230000031700 light absorption Effects 0.000 claims 1
- 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 17
- 210000004369 blood Anatomy 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229930185723 monacolin Natural products 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000001888 Peptone Substances 0.000 description 3
- 108010080698 Peptones Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 235000019319 peptone Nutrition 0.000 description 3
- 239000013587 production medium Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- -1 sutucarose Chemical compound 0.000 description 2
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 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 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 239000013586 microbial product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Obesity (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Priority Applications (32)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54017856A JPS5925599B2 (ja) | 1979-02-20 | 1979-02-20 | 新生理活性物質モナコリンｋおよびその製造法 |
| AU55673/80A AU532626B2 (en) | 1979-02-20 | 1980-02-19 | Monacolink |
| CA345,983A CA1129794A (en) | 1979-02-20 | 1980-02-19 | Antihypercholesteraemic agent, monacolin k, and its preparation |
| IE321/80A IE49743B1 (en) | 1979-02-20 | 1980-02-19 | Antihypercholesteraemic agent,monacolin k,and its preparation |
| KR1019800000654A KR830002801B1 (ko) | 1979-02-20 | 1980-02-19 | 고(高) 콜레스테롤혈증치료제, 모나콜린 k의 제조방법 |
| PL1980222120A PL124304B1 (en) | 1979-02-20 | 1980-02-20 | Process for preparing novel 1-/alpha-methylbutyryloxy/-3,7-dimethyl-8-/2-/2-keto-4-hydroxytetrahydropyran-6-yl/-ethyl/-1,2,3,7-8,8a-hexahydronaphtalene |
| HU80397A HU182069B (en) | 1979-02-20 | 1980-02-20 | Process for preparing monacoline k, a compound with antihypercholesteremic activity |
| NZ192919A NZ192919A (en) | 1979-02-20 | 1980-02-20 | Monacolin k and pharmaceutical compositions |
| MX808652U MX6314E (es) | 1979-02-20 | 1980-02-20 | Procedimiento microbiologico para la preparacion de monacolin k |
| DE3006216A DE3006216C2 (de) | 1979-02-20 | 1980-02-20 | Monacolin K, Verfahren zu dessen Herstellung und diese Verbindung enthaltende Arzneimittel |
| SU802887300A SU1158048A3 (ru) | 1979-02-20 | 1980-02-20 | Способ получени монаколина @ ,обладающего антигиперхолестеримическим действием |
| ES488796A ES8103171A1 (es) | 1979-02-20 | 1980-02-20 | Un procedimiento de preparacion de monacolina k. |
| AT0092980A AT373915B (de) | 1979-02-20 | 1980-02-20 | Verfahren zum herstellen von neuem monacolin k |
| FI800506A FI66427C (fi) | 1979-02-20 | 1980-02-20 | Foerfarande foer framstaellning av en ny som laekemedel anvaendbar foerening monacolin k |
| SE8001339A SE453301B (sv) | 1979-02-20 | 1980-02-20 | Antihyperkolesterolemiskt medel, monakolin k, forfarande for framstellning derav samt farmaceutisk komposition innehallande detsamma |
| IT67262/80A IT1175260B (it) | 1979-02-20 | 1980-02-20 | Agente anti ipercolesterolemico e procedimento per la sua preparazione |
| DD80219159A DD154494A5 (de) | 1979-02-20 | 1980-02-20 | Verfahren zur herstellung von monacolin k |
| FR8003662A FR2449685B1 (fr) | 1979-02-20 | 1980-02-20 | Agent antihypercholesterolemique prepare par culture de microorganismes du genre monascus et son procede de preparation |
| DK73080A DK149095C (da) | 1979-02-20 | 1980-02-20 | Fremgangsmaade til fremstilling af en cholesterolsynteseinhiberende forbindelse kaldet monacolin k |
| NL8001041A NL191540C (nl) | 1979-02-20 | 1980-02-20 | Verbinding met antihypercholesteremische werkzaamheid, alsmede farmaceutisch preparaat dat deze verbinding bevat. |
| DE3051175A DE3051175C2 (OSRAM) | 1979-02-20 | 1980-02-20 | |
| PH23668A PH15145A (en) | 1979-02-20 | 1980-02-20 | Antihypercholesteraemic agent,monacolin k.process for the production and compositions containing same |
| NO800451A NO153974C (no) | 1979-02-20 | 1980-02-20 | Fremgangsmaate til fremstilling av forbindelsen monacolin k |
| CH136680A CH645890A5 (de) | 1979-02-20 | 1980-02-20 | Monacolin k, seine herstellung und dieses enthaltendes antihypercholesterinaemisches mittel. |
| BE0/199476A BE881825A (fr) | 1979-02-20 | 1980-02-20 | Agent antihypercholesterolemique prepare par culture de micro-organismes du genre monascus et son procede de preparation |
| ZA00800962A ZA80962B (en) | 1979-02-20 | 1980-02-20 | Antihypercholesteraemic agent,monacolin k,and its preparation |
| GB8005748A GB2046737B (en) | 1979-02-20 | 1980-02-20 | Antihypercholesteraemic agent monacolin k and its preparation |
| SU802977031A SU969702A1 (ru) | 1979-02-20 | 1980-09-12 | Монаколин К, обладающий гипохолестеримическим действием |
| SG67/84A SG6784G (en) | 1979-02-20 | 1984-01-24 | Antihypercholesteraemic agent,monacolin k,and its preparation |
| DK47085A DK165990C (da) | 1979-02-20 | 1985-02-01 | Fremgangsmaade til fremstilling af carboxylsyren af en cholesterolsynteseinhiberende forbindelse kaldet monacolin k eller salte deraf |
| DK021889A DK21889A (da) | 1979-02-20 | 1989-01-18 | Anvendelse af monacolin k, den tilsvarende carboxylsyreforbindelse eller salte af carboxylsyren til fremstilling af et laegemiddel til behandling af hypercholesterolaemi |
| MX9203568A MX9203568A (es) | 1979-02-20 | 1992-06-26 | Agente antihipercolesteremico, monacolina k, y su preparacion. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54017856A JPS5925599B2 (ja) | 1979-02-20 | 1979-02-20 | 新生理活性物質モナコリンｋおよびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55111790A JPS55111790A (en) | 1980-08-28 |
| JPS5925599B2 true JPS5925599B2 (ja) | 1984-06-19 |
Family
ID=11955290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54017856A Expired JPS5925599B2 (ja) | 1979-02-20 | 1979-02-20 | 新生理活性物質モナコリンｋおよびその製造法 |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5925599B2 (OSRAM) |
| KR (1) | KR830002801B1 (OSRAM) |
| AT (1) | AT373915B (OSRAM) |
| AU (1) | AU532626B2 (OSRAM) |
| BE (1) | BE881825A (OSRAM) |
| CA (1) | CA1129794A (OSRAM) |
| CH (1) | CH645890A5 (OSRAM) |
| DD (1) | DD154494A5 (OSRAM) |
| DE (2) | DE3006216C2 (OSRAM) |
| DK (2) | DK149095C (OSRAM) |
| ES (1) | ES8103171A1 (OSRAM) |
| FI (1) | FI66427C (OSRAM) |
| FR (1) | FR2449685B1 (OSRAM) |
| GB (1) | GB2046737B (OSRAM) |
| HU (1) | HU182069B (OSRAM) |
| IE (1) | IE49743B1 (OSRAM) |
| IT (1) | IT1175260B (OSRAM) |
| MX (1) | MX6314E (OSRAM) |
| NL (1) | NL191540C (OSRAM) |
| NO (1) | NO153974C (OSRAM) |
| NZ (1) | NZ192919A (OSRAM) |
| PH (1) | PH15145A (OSRAM) |
| PL (1) | PL124304B1 (OSRAM) |
| SE (1) | SE453301B (OSRAM) |
| SG (1) | SG6784G (OSRAM) |
| SU (2) | SU1158048A3 (OSRAM) |
| ZA (1) | ZA80962B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022135089A (ja) * | 2021-03-04 | 2022-09-15 | 小林製薬株式会社 | コレステロールの低減剤 |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55150898A (en) * | 1979-05-11 | 1980-11-25 | Sankyo Co Ltd | Preparation of a new physiologically active substance mb-530b |
| US4231938A (en) * | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| JPS5621594A (en) * | 1979-07-27 | 1981-02-28 | Sankyo Co Ltd | Mb-530b carboxylic acid metal salt and its preparation |
| PT72394B (en) * | 1980-02-04 | 1982-09-06 | Merck & Co Inc | Process for preparing dihydro and tetrahydromevinoline hypocholesterolimics |
| AU548996B2 (en) * | 1980-02-04 | 1986-01-09 | Merck & Co., Inc. | Tetrahydro-2h-pyran-2-one derivatives |
| JPH0692381B2 (ja) * | 1980-03-31 | 1994-11-16 | 三共株式会社 | Ｍｂ−５３０ａ誘導体 |
| JPS56142236A (en) | 1980-04-08 | 1981-11-06 | Sankyo Co Ltd | Ml-236a and mb-530a derivative |
| MX7065E (es) * | 1980-06-06 | 1987-04-10 | Sankyo Co | Un procedimiento microbiologico para preparar derivados de ml-236b |
| JPS5835144A (ja) * | 1981-08-27 | 1983-03-01 | Sankyo Co Ltd | Ｍｂ−５３０ｂ誘導体およびその製造法 |
| US4782084A (en) * | 1987-06-29 | 1988-11-01 | Merck & Co., Inc. | HMG-COA reductase inhibitors |
| US4997848A (en) * | 1987-10-27 | 1991-03-05 | Sankyo Company, Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition |
| CA2062023A1 (en) * | 1992-02-10 | 1993-08-11 | Jagroop S. Dahiya | Novel fungal strains and use thereof in antibiotic production |
| WO1993017991A1 (en) * | 1992-03-04 | 1993-09-16 | Fujisawa Pharmaceutical Co., Ltd. | TETRALIN DERIVATIVES AS HMG-CoA REDUCTASE INHIBITORS |
| NZ247617A (en) | 1992-05-15 | 1995-07-26 | Sankyo Co | Octahydronaphthalene oxime derivatives and pharmaceutical compositions |
| US6812007B1 (en) * | 1992-11-04 | 2004-11-02 | Keri Vilmos | Process for the isolation and purification of mevinolin |
| HU210867B (en) * | 1992-11-04 | 1995-10-30 | Biogal Gyogyszergyar | Method for extraction and purification of mevinolin from culture medium |
| SI9300303A (en) * | 1993-06-08 | 1994-12-31 | Krka Tovarna Zdravil | Process for isolation of hypolipemic effective substance |
| US5409820A (en) * | 1993-08-06 | 1995-04-25 | Apotex, Inc. | Process for the production of lovastatin using Coniothyrium fuckelii |
| US7238348B2 (en) | 1996-09-30 | 2007-07-03 | Beijing Peking University Wbl Corporation Ltd. | Method of treatment of osteoporosis with compositions of red rice fermentation products |
| US6046022A (en) | 1996-09-30 | 2000-04-04 | Peking University | Methods and compositions employing red rice fermentation products |
| JP2001527424A (ja) | 1998-03-20 | 2001-12-25 | ビオガル・ジョージィセルジャール・エル・テー | ロバスタチンヒドロキシ酸を製造するための代謝コントロール発酵操作 |
| PL357946A1 (en) | 2000-02-24 | 2004-08-09 | Biogal Gyogyszergyar Rt | Method of purifying a fermentation broth |
| EP1265884A4 (en) | 2000-03-03 | 2003-05-21 | Plus Chemical S A | PROCESS FOR THE PURIFICATION OF LOVASTATIN AND SIMVASTATIN FOR REDUCING THE CONTENT OF DIMER IMPURITIES |
| KR20010095780A (ko) * | 2000-04-12 | 2001-11-07 | 나가오카 마사시 | 배아 홍국 |
| IN192861B (OSRAM) | 2000-06-30 | 2004-05-22 | Ranbaxy Lab Ltd | |
| DE60218822T2 (de) * | 2001-02-09 | 2007-07-12 | Unilever N.V. | Nahrungsmittel enthaltend sojaprotein und statin |
| KR100379075B1 (en) | 2002-03-07 | 2003-04-08 | Jinis Biopharmaceuticals Co | Method for producing low cholesterol animal food product and food product therefrom |
| KR20020093147A (ko) * | 2002-05-30 | 2002-12-13 | 지니스생명공학 주식회사 | 성인병 예방 및 치료 보조제 |
| KR100710500B1 (ko) | 2005-05-18 | 2007-04-24 | 고려대학교 산학협력단 | 홍국균을 이용한 모나콜린 ｋ 생산방법 |
| EP2327682A1 (en) | 2009-10-29 | 2011-06-01 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| EP2373609B1 (en) | 2008-12-19 | 2013-10-16 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| RO128803A0 (ro) | 2012-10-12 | 2013-09-30 | Ion Gigel Fulga | Compoziţie pentru tratamentul sau prevenirea dislipidemiilor |
| CN110331151A (zh) * | 2019-04-11 | 2019-10-15 | 北京工商大学 | 紫色红曲菌mokH基因过表达菌株的构建方法 |
| CN111297938A (zh) * | 2020-03-11 | 2020-06-19 | 北京康立生医药技术开发有限公司 | 一种辅助降血脂组合物中洛伐他汀的检测方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612114B2 (OSRAM) * | 1974-06-07 | 1981-03-18 | ||
| JPS55150898A (en) * | 1979-05-11 | 1980-11-25 | Sankyo Co Ltd | Preparation of a new physiologically active substance mb-530b |
| IL60219A (en) * | 1979-06-15 | 1985-05-31 | Merck & Co Inc | Hypocholesteremic fermentation products of the hmg-coa reductase inhibitor type,their preparation and pharmaceutical compositions containing them |
-
1979
- 1979-02-20 JP JP54017856A patent/JPS5925599B2/ja not_active Expired
-
1980
- 1980-02-19 KR KR1019800000654A patent/KR830002801B1/ko not_active Expired
- 1980-02-19 CA CA345,983A patent/CA1129794A/en not_active Expired
- 1980-02-19 AU AU55673/80A patent/AU532626B2/en not_active Expired
- 1980-02-19 IE IE321/80A patent/IE49743B1/en not_active IP Right Cessation
- 1980-02-20 ZA ZA00800962A patent/ZA80962B/xx unknown
- 1980-02-20 NO NO800451A patent/NO153974C/no unknown
- 1980-02-20 HU HU80397A patent/HU182069B/hu unknown
- 1980-02-20 CH CH136680A patent/CH645890A5/de not_active IP Right Cessation
- 1980-02-20 DD DD80219159A patent/DD154494A5/de unknown
- 1980-02-20 IT IT67262/80A patent/IT1175260B/it active
- 1980-02-20 MX MX808652U patent/MX6314E/es unknown
- 1980-02-20 SU SU802887300A patent/SU1158048A3/ru active
- 1980-02-20 FR FR8003662A patent/FR2449685B1/fr not_active Expired
- 1980-02-20 FI FI800506A patent/FI66427C/fi not_active IP Right Cessation
- 1980-02-20 AT AT0092980A patent/AT373915B/de not_active IP Right Cessation
- 1980-02-20 NL NL8001041A patent/NL191540C/xx not_active IP Right Cessation
- 1980-02-20 PL PL1980222120A patent/PL124304B1/pl unknown
- 1980-02-20 GB GB8005748A patent/GB2046737B/en not_active Expired
- 1980-02-20 DE DE3006216A patent/DE3006216C2/de not_active Expired
- 1980-02-20 SE SE8001339A patent/SE453301B/sv not_active IP Right Cessation
- 1980-02-20 ES ES488796A patent/ES8103171A1/es not_active Expired
- 1980-02-20 NZ NZ192919A patent/NZ192919A/en unknown
- 1980-02-20 BE BE0/199476A patent/BE881825A/fr not_active IP Right Cessation
- 1980-02-20 PH PH23668A patent/PH15145A/en unknown
- 1980-02-20 DE DE3051175A patent/DE3051175C2/de not_active Expired
- 1980-02-20 DK DK73080A patent/DK149095C/da not_active IP Right Cessation
- 1980-09-12 SU SU802977031A patent/SU969702A1/ru active
-
1984
- 1984-01-24 SG SG67/84A patent/SG6784G/en unknown
-
1989
- 1989-01-18 DK DK021889A patent/DK21889A/da not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022135089A (ja) * | 2021-03-04 | 2022-09-15 | 小林製薬株式会社 | コレステロールの低減剤 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5925599B2 (ja) | 新生理活性物質モナコリンｋおよびその製造法 | |
| CA2127878C (en) | Fo-1289 substance and its production | |
| EP0099692A1 (en) | New furanone derivatives, process for the preparation thereof and use thereof | |
| JPH06234693A (ja) | 新規イソテトラセノン系物質及びその製造法 | |
| JPS6113798B2 (OSRAM) | ||
| JPS5814439B2 (ja) | 新規化合物フレノリシンｂおよびその製造法 | |
| NL8204904A (nl) | Dihydro- en tetrahydromonacolin l, metaalzouten en alkylesters daarvan, alsmede werkwijze voor het bereiden ervan. | |
| JP3026864B2 (ja) | 新規セスキテルペン誘導体 | |
| JPS6210998B2 (OSRAM) | ||
| JPS62132878A (ja) | 新生理活性物質モナコリンｍ及びその製造法 | |
| EP0629184A1 (en) | TETRALIN DERIVATIVES AS HMG-CoA REDUCTASE INHIBITORS | |
| JPS58109480A (ja) | 新生理活性物質ジヒドロモナコリンｌ及びその製造法 | |
| JPH08127583A (ja) | Ｆｏ−２０４７物質およびその製造法 | |
| JPH04243894A (ja) | 新規ｑ−６４０２化合物およびその製造法 | |
| JPS5840475B2 (ja) | 新生理活性物質ｍｌ−２３６ａおよびその製造法 | |
| JPS5945360B2 (ja) | 生理活性物質ｍｌ−２３６ｂの製造法 | |
| JPH03227971A (ja) | カルバゾール化合物 | |
| JPS5889187A (ja) | Ｎｏ１４−ａ物質およびその製造法 | |
| JPH06157520A (ja) | 新規物質ｈｑ２４ | |
| JPH064634B2 (ja) | 新規化合物ｗｆ１３６０類、その製造法およびその用途 | |
| JPS63122687A (ja) | 新規ナフトキノン系化合物ｎｑｙ | |
| JPH0359911B2 (OSRAM) | ||
| JPH08176179A (ja) | 新規生理活性物質ｎａ２３０６３ａ、その製造法及びその用途 | |
| JPH02255655A (ja) | 新規生理活性物質ｄｃ１１８ | |
| JPS5948991B2 (ja) | 抗生物質ｓｆ−８３７ｍ↓１物質の製造法 |