JPS5810572A - Ｍｌ−２３６ｂ誘導体およびその製造法 - Google Patents
Ｍｌ−２３６ｂ誘導体およびその製造法Info
- Publication number
- JPS5810572A JPS5810572A JP10596781A JP10596781A JPS5810572A JP S5810572 A JPS5810572 A JP S5810572A JP 10596781 A JP10596781 A JP 10596781A JP 10596781 A JP10596781 A JP 10596781A JP S5810572 A JPS5810572 A JP S5810572A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- derivative
- represented
- pharmacologically acceptable
- compound
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical class 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 claims abstract description 28
- -1 ML-236B carboxylic acid Chemical class 0.000 claims abstract description 26
- 150000002596 lactones Chemical class 0.000 claims abstract description 20
- 239000000284 extract Substances 0.000 claims abstract description 16
- 244000005700 microbiome Species 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 241001450911 Circinella Species 0.000 claims description 3
- 241001450909 Gongronella Species 0.000 claims description 3
- 241000186046 Actinomyces Species 0.000 claims description 2
- 241000235400 Phycomyces Species 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 241000699666 Mus <mouse, genus> Species 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 abstract description 19
- 241000235395 Mucor Species 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 10
- 235000012000 cholesterol Nutrition 0.000 abstract description 9
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 241000235527 Rhizopus Species 0.000 abstract description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract description 2
- 150000002632 lipids Chemical class 0.000 abstract description 2
- 206010003210 Arteriosclerosis Diseases 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 201000005577 familial hyperlipidemia Diseases 0.000 abstract 1
- 239000001963 growth medium Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 230000000813 microbial effect Effects 0.000 description 6
- 241000187747 Streptomyces Species 0.000 description 5
- 241000736854 Syncephalastrum Species 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 241000235389 Absidia Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000019687 Lamb Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 239000013028 medium composition Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000009629 microbiological culture Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- FVTWJXMFYOXOKK-UHFFFAOYSA-N 2-fluoroacetamide Chemical compound NC(=O)CF FVTWJXMFYOXOKK-UHFFFAOYSA-N 0.000 description 1
- 241000235390 Absidia glauca Species 0.000 description 1
- 240000005007 Actinomucor elegans Species 0.000 description 1
- 235000013650 Actinomucor elegans Nutrition 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000467320 Circinella muscae Species 0.000 description 1
- 241001450910 Circinella umbellata Species 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- 241001450899 Gongronella butleri Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001231445 Mucor durus Species 0.000 description 1
- 241000907556 Mucor hiemalis Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241000813867 Streptomyces roseochromogenus Species 0.000 description 1
- 241000041999 Trametes coccinea Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10596781A JPS5810572A (ja) | 1981-07-07 | 1981-07-07 | Ｍｌ−２３６ｂ誘導体およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10596781A JPS5810572A (ja) | 1981-07-07 | 1981-07-07 | Ｍｌ−２３６ｂ誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5810572A true JPS5810572A (ja) | 1983-01-21 |
| JPH0354103B2 JPH0354103B2 (enrdf_load_stackoverflow) | 1991-08-19 |
Family
ID=14421547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10596781A Granted JPS5810572A (ja) | 1981-07-07 | 1981-07-07 | Ｍｌ−２３６ｂ誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5810572A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0314435A2 (en) | 1987-10-27 | 1989-05-03 | Sankyo Company Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition, processes for their preparation and compositions containing them |
| US5451688A (en) * | 1992-12-28 | 1995-09-19 | Sankyo Company, Limited | Hexahydronaphthalene ester derivatives, their preparation and their therapeutic uses |
| US6696599B2 (en) | 1999-02-03 | 2004-02-24 | Institute For Drug Research, Ltd. | Microbial process for preparing pravastatin |
| US6905851B1 (en) | 1999-07-12 | 2005-06-14 | Ivax Drug Research Institute | Hydroxylation of compactin pravastatin by micromonospora |
| US7504244B2 (en) | 2004-12-03 | 2009-03-17 | TEVA Gyógyszergyár Zártkörúen Múködó Részvénytársaság | Process for constructing strain having compactin hydroxylation ability |
-
1981
- 1981-07-07 JP JP10596781A patent/JPS5810572A/ja active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0314435A2 (en) | 1987-10-27 | 1989-05-03 | Sankyo Company Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition, processes for their preparation and compositions containing them |
| US5451688A (en) * | 1992-12-28 | 1995-09-19 | Sankyo Company, Limited | Hexahydronaphthalene ester derivatives, their preparation and their therapeutic uses |
| US5827855A (en) * | 1992-12-28 | 1998-10-27 | Sankyo Company, Limited | Hexahydronaphthalene ester derivatives their preparation and their therapeutic uses |
| US6696599B2 (en) | 1999-02-03 | 2004-02-24 | Institute For Drug Research, Ltd. | Microbial process for preparing pravastatin |
| US6750366B2 (en) | 1999-02-03 | 2004-06-15 | Institute For Drug Research Ltd. | Microbial process for preparing pravastatin |
| US6905851B1 (en) | 1999-07-12 | 2005-06-14 | Ivax Drug Research Institute | Hydroxylation of compactin pravastatin by micromonospora |
| US7504244B2 (en) | 2004-12-03 | 2009-03-17 | TEVA Gyógyszergyár Zártkörúen Múködó Részvénytársaság | Process for constructing strain having compactin hydroxylation ability |
| US7700752B2 (en) | 2004-12-03 | 2010-04-20 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Process for constructing strain having compactin hydroxylation ability |
| US7700337B2 (en) | 2004-12-03 | 2010-04-20 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Process for constructing strain having compactin hydroxylation ability |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0354103B2 (enrdf_load_stackoverflow) | 1991-08-19 |
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