CH647749A5 - Salze und ester von monacolin-k, verfahren zu ihrer herstellung und pharmazeutische praeparate. - Google Patents
Salze und ester von monacolin-k, verfahren zu ihrer herstellung und pharmazeutische praeparate. Download PDFInfo
- Publication number
- CH647749A5 CH647749A5 CH5736/80A CH573680A CH647749A5 CH 647749 A5 CH647749 A5 CH 647749A5 CH 5736/80 A CH5736/80 A CH 5736/80A CH 573680 A CH573680 A CH 573680A CH 647749 A5 CH647749 A5 CH 647749A5
- Authority
- CH
- Switzerland
- Prior art keywords
- monacolin
- monascus
- sank
- salts
- group
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 8
- 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 claims description 100
- 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 claims description 66
- -1 phenacyl group Chemical group 0.000 claims description 43
- 241000031003 Monascus ruber Species 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 28
- 244000005700 microbiome Species 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000001963 growth medium Substances 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 241000228347 Monascus <ascomycete fungus> Species 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 244000113306 Monascus purpureus Species 0.000 claims description 3
- 235000002322 Monascus purpureus Nutrition 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229930185723 monacolin Natural products 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 241000409281 Monascus paxii Species 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005354 acylalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 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 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 238000000855 fermentation Methods 0.000 description 16
- 230000004151 fermentation Effects 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000002609 medium Substances 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
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- 230000015572 biosynthetic process Effects 0.000 description 10
- 235000012000 cholesterol Nutrition 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011160 research Methods 0.000 description 9
- 229920001817 Agar Polymers 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
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- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 5
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
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- 101150041968 CDC13 gene Proteins 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 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 3
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
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- 239000011324 bead Substances 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
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940057059 monascus purpureus Drugs 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000005868 ontogenesis Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9581479A JPS5621594A (en) | 1979-07-27 | 1979-07-27 | Mb-530b carboxylic acid metal salt and its preparation |
| JP12346179A JPS5646841A (en) | 1979-09-26 | 1979-09-26 | Mb-530b carboxylic acid ester and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH647749A5 true CH647749A5 (de) | 1985-02-15 |
Family
ID=26436995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5736/80A CH647749A5 (de) | 1979-07-27 | 1980-07-25 | Salze und ester von monacolin-k, verfahren zu ihrer herstellung und pharmazeutische praeparate. |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT375334B (OSRAM) |
| AU (1) | AU6083980A (OSRAM) |
| CH (1) | CH647749A5 (OSRAM) |
| DD (1) | DD153827A5 (OSRAM) |
| DE (1) | DE3028284A1 (OSRAM) |
| DK (1) | DK322380A (OSRAM) |
| ES (1) | ES493726A0 (OSRAM) |
| FI (1) | FI71300C (OSRAM) |
| FR (1) | FR2462417A1 (OSRAM) |
| GB (1) | GB2055100A (OSRAM) |
| IT (1) | IT1147763B (OSRAM) |
| NL (1) | NL8004303A (OSRAM) |
| NO (1) | NO156210C (OSRAM) |
| NZ (1) | NZ194445A (OSRAM) |
| PL (1) | PL225901A1 (OSRAM) |
| SE (1) | SE445828B (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1327360C (en) * | 1983-11-14 | 1994-03-01 | William F. Hoffman | Oxo-analogs of mevinolin-like antihypercholesterolemic agents |
| DE3580863D1 (de) * | 1984-06-04 | 1991-01-24 | Merck & Co Inc | Herstellungsverfahren von hemmstoffen der hmg-coa-reduktase mit einer 3,5-dihydroxypentanoatteilstruktur. |
| EP0204287A3 (en) * | 1985-06-04 | 1987-07-01 | Merck & Co. Inc. | Process for the preparation of hmg-coa reductase inhibitors with a 3,5-dihydroxypentanoate subunit |
| USRE33033E (en) * | 1985-07-05 | 1989-08-22 | Merck & Co., Inc. | Process for the preparation of HMG-CoA reductase inhibitors intermediates |
| US4611081A (en) * | 1985-07-05 | 1986-09-09 | Merck & Co., Inc. | Process for the preparation of HMG-CoA reductase inhibitors intermediates |
| US6046022A (en) | 1996-09-30 | 2000-04-04 | Peking University | Methods and compositions employing red rice fermentation products |
| 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 |
| JP2002518448A (ja) * | 1998-06-24 | 2002-06-25 | メルク エンド カムパニー インコーポレーテッド | 高血中コレステロールを治療する組成物および方法 |
| SI20070A (sl) | 1998-09-18 | 2000-04-30 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Nove soli inhibitorjev HMG-CoA reduktaze |
| SK16982002A3 (sk) * | 2000-06-09 | 2003-04-01 | Lek Pharmaceuticals D. D. | Stabilizovaná farmaceuticky účinná kompozícia a liečivý prípravok túto kompozíciu obsahujúci |
| US6806290B2 (en) | 2000-06-09 | 2004-10-19 | Lek Pharmaceuticals D.D. | Stabilized pharmaceutically effective composition and pharmaceutical formulation comprising the same |
| WO2002020457A1 (en) * | 2000-09-06 | 2002-03-14 | Merck & Co., Inc. | Dihydroxy open-acid salt of simvastatin |
| WO2002100323A2 (en) | 2001-06-13 | 2002-12-19 | Ranbaxy Laboratories Limited | METHYL ANALOGS OF SIMVASTATIN AS NOVEL HMG-CoA REDUCTASE INHIBITORS |
| KR100379075B1 (en) | 2002-03-07 | 2003-04-08 | Jinis Biopharmaceuticals Co | Method for producing low cholesterol animal food product and food product therefrom |
| US8158362B2 (en) | 2005-03-30 | 2012-04-17 | Decode Genetics Ehf. | Methods of diagnosing susceptibility to myocardial infarction and screening for an LTA4H haplotype |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4137322A (en) * | 1976-11-02 | 1979-01-30 | Sankyo Company Limited | ML-236B carboxylic acid derivatives and their use as antihyperlipemic agents |
| JPS55150898A (en) * | 1979-05-11 | 1980-11-25 | Sankyo Co Ltd | Preparation of a new physiologically active substance mb-530b |
-
1980
- 1980-07-24 ES ES493726A patent/ES493726A0/es active Granted
- 1980-07-25 FR FR8016452A patent/FR2462417A1/fr active Granted
- 1980-07-25 NZ NZ194445A patent/NZ194445A/en unknown
- 1980-07-25 DE DE19803028284 patent/DE3028284A1/de active Granted
- 1980-07-25 NO NO802244A patent/NO156210C/no unknown
- 1980-07-25 FI FI802357A patent/FI71300C/fi not_active IP Right Cessation
- 1980-07-25 CH CH5736/80A patent/CH647749A5/de not_active IP Right Cessation
- 1980-07-25 DK DK322380A patent/DK322380A/da not_active Application Discontinuation
- 1980-07-25 SE SE8005386A patent/SE445828B/sv not_active IP Right Cessation
- 1980-07-26 PL PL22590180A patent/PL225901A1/xx unknown
- 1980-07-27 NL NL8004303A patent/NL8004303A/nl not_active Application Discontinuation
- 1980-07-28 GB GB8024665A patent/GB2055100A/en not_active Withdrawn
- 1980-07-28 IT IT68211/80A patent/IT1147763B/it active
- 1980-07-28 AT AT0392380A patent/AT375334B/de not_active IP Right Cessation
- 1980-07-28 DD DD80222916A patent/DD153827A5/de unknown
- 1980-07-28 AU AU60839/80A patent/AU6083980A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FI71300C (fi) | 1986-12-19 |
| GB2055100A (en) | 1981-02-25 |
| NO156210C (no) | 1987-08-12 |
| DK322380A (da) | 1981-01-28 |
| AU6083980A (en) | 1981-01-29 |
| NO802244L (no) | 1981-01-28 |
| DE3028284A1 (de) | 1981-02-19 |
| FR2462417B1 (OSRAM) | 1984-01-20 |
| PL225901A1 (OSRAM) | 1982-07-19 |
| DD153827A5 (de) | 1982-02-03 |
| FI802357A7 (fi) | 1981-01-28 |
| AT375334B (de) | 1984-07-25 |
| FR2462417A1 (fr) | 1981-02-13 |
| SE8005386L (sv) | 1981-01-28 |
| IT1147763B (it) | 1986-11-26 |
| ES8105781A1 (es) | 1981-06-16 |
| ATA392380A (de) | 1983-12-15 |
| NZ194445A (en) | 1984-07-06 |
| DE3028284C2 (OSRAM) | 1990-08-09 |
| ES493726A0 (es) | 1981-06-16 |
| NO156210B (no) | 1987-05-04 |
| NL8004303A (nl) | 1981-01-29 |
| IT8068211A0 (it) | 1980-07-28 |
| FI71300B (fi) | 1986-09-09 |
| SE445828B (sv) | 1986-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |