JPS6113699B2 - - Google Patents
Info
- Publication number
- JPS6113699B2 JPS6113699B2 JP7612780A JP7612780A JPS6113699B2 JP S6113699 B2 JPS6113699 B2 JP S6113699B2 JP 7612780 A JP7612780 A JP 7612780A JP 7612780 A JP7612780 A JP 7612780A JP S6113699 B2 JPS6113699 B2 JP S6113699B2
- Authority
- JP
- Japan
- Prior art keywords
- solution
- methanol
- formula
- acetone
- solvent
- 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
- 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 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000282472 Canis lupus familiaris Species 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
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA 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)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 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
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 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 1
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 1
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 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
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography 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
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004108 freeze drying Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7612780A JPS572240A (en) | 1980-06-06 | 1980-06-06 | Ml-236b derivative |
| MX819478U MX7065E (es) | 1980-06-06 | 1981-06-04 | Un procedimiento microbiologico para preparar derivados de ml-236b |
| DK247081A DK149080C (da) | 1980-06-06 | 1981-06-04 | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| IT67777/81A IT1144598B (it) | 1980-06-06 | 1981-06-05 | Composti farmaceutici atti ad inibire la biosintesi del colesterolo e procedimento per la loro preparazione |
| NL8102737A NL191738C (nl) | 1980-06-06 | 1981-06-05 | ML-236B-derivaten, werkwijze voor hun bereiding en farmaceutische preparaten, die deze derivaten bevatten. |
| CH3722/81A CH655090A5 (de) | 1980-06-06 | 1981-06-05 | Hexahydronaphthalinderivate und ihre herstellung. |
| FI811762A FI71168C (fi) | 1980-06-06 | 1981-06-05 | Foerfarande foer framstaellning av ml-236b-derivat vilka anvaends som laekemedel |
| DE19813122499 DE3122499A1 (de) | 1980-06-06 | 1981-06-05 | Neue derivate von ml-236b, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittelzubereitungen |
| AU71376/81A AU549988B2 (en) | 1980-06-06 | 1981-06-05 | Hydroxy esters |
| FR8111190A FR2483912B1 (fr) | 1980-06-06 | 1981-06-05 | Derives hydroxycarboxyles du compose ml-236b, leur procede de preparation et leur application therapeutique |
| KR1019810002023A KR840001055B1 (ko) | 1980-06-06 | 1981-06-05 | Ml-236b 유도체의 제조방법 |
| US06/270,846 US4346227A (en) | 1980-06-06 | 1981-06-05 | ML-236B Derivatives and their preparation |
| SE8103560A SE453389B (sv) | 1980-06-06 | 1981-06-05 | Hydroxikarboxylsyror, ringslutna laktoner, salter och estrar derav samt forfarande for framstellning av nemnda foreningar |
| IE1257/81A IE51270B1 (en) | 1980-06-06 | 1981-06-05 | Ml-236b derivatives and their preparation |
| ES502827A ES8300353A1 (es) | 1980-06-06 | 1981-06-05 | Procedimiento de preparar acidos hidroxicarboxilicos y sus derivados. |
| CA000379232A CA1150170A (en) | 1980-06-06 | 1981-06-08 | Ml-236b derivatives and their preparation |
| GB8117450A GB2077264B (en) | 1980-06-06 | 1981-06-08 | Ml-236b derivatives and their preparation |
| BE0/205046A BE889150A (fr) | 1980-06-06 | 1981-06-09 | Derives hydroxycarboxyles du compose ml-236b, leur procede de preparation et leur application therapeutique |
| AT0256781A AT374495B (de) | 1980-06-06 | 1981-06-09 | Verfahren zur herstellung neuer derivate der verbindung ml-236b |
| US06/351,975 US4448979A (en) | 1980-06-06 | 1982-02-24 | ML-236B Derivatives |
| US06/351,974 US4410629A (en) | 1980-06-06 | 1982-02-24 | ML-236B Derivatives and their preparation |
| MX9203563A MX9203563A (es) | 1980-06-06 | 1992-06-26 | Derivados de ml-236b y su preparacion. |
| NL960028C NL960028I2 (nl) | 1980-06-06 | 1996-11-18 | ML-236B-derivaten, werkwijze voor hun bereiding enfarmaceutische preparaten, die deze derivaten bevatten. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7612780A JPS572240A (en) | 1980-06-06 | 1980-06-06 | Ml-236b derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572240A JPS572240A (en) | 1982-01-07 |
| JPS6113699B2 true JPS6113699B2 (enrdf_load_stackoverflow) | 1986-04-15 |
Family
ID=13596258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7612780A Granted JPS572240A (en) | 1980-06-06 | 1980-06-06 | Ml-236b derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS572240A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008102563A1 (ja) | 2007-02-23 | 2008-08-28 | Next21 K.K. | 血管攣縮の治療剤又は予防剤 |
| WO2010041619A1 (ja) | 2008-10-06 | 2010-04-15 | メルシャン株式会社 | シュードノカルディア・オートトロフィカ（Pseudonocardia autotrophica）発現ベクター |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61158237A (ja) * | 1984-12-28 | 1986-07-17 | Sony Corp | デ−タ通信方法 |
| JPS62227236A (ja) * | 1986-03-29 | 1987-10-06 | Omron Tateisi Electronics Co | 複数の装置相互間のデ−タ伝送システム |
| JPH0251582A (ja) * | 1988-08-12 | 1990-02-21 | Kyokado Eng Co Ltd | 地盤注入用薬液 |
| SI20305A (sl) * | 1999-08-06 | 2001-02-28 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Kristali natrijeve soli pravastatina |
| IL142619A (en) | 2000-04-18 | 2008-03-20 | Daiichi Sankyo Co Ltd | Gardens from a cluster of gardens |
| AU2002211462A1 (en) * | 2000-10-05 | 2002-04-22 | Teva Gyogyszergyar Reszvenytarsasag | Pravastatin sodium substantially free of pravastatin lactone and epi-pravastatin, and compositions containing same |
| AU2004298375A1 (en) * | 2003-12-17 | 2005-06-30 | Dainippon Sumitomo Pharma Co., Ltd. | Medicinal compositions and combinations |
| CA2585623C (en) | 2004-10-27 | 2012-06-05 | Daiichi Sankyo Company Limited | Ortho-substituted benzene derivatives |
| WO2008001499A1 (fr) | 2006-06-29 | 2008-01-03 | Kowa Co., Ltd. | Agent prophylactique et/ou thérapeutique pour le traitement de la polyarthrite rhumatoïde |
| ES2425969T3 (es) | 2007-04-27 | 2013-10-18 | Kyushu University, National University Corporation | Agente para el tratamiento de enfermedades pulmonares |
| US20130115622A1 (en) | 2009-12-14 | 2013-05-09 | Kyoto University | Pharmaceutical composition for prevention and treatment of amyotrophic lateral sclerosis |
| JP6536871B2 (ja) | 2013-12-02 | 2019-07-03 | 国立大学法人京都大学 | Ｆｇｆｒ３病の予防および治療剤ならびにそのスクリーニング方法 |
| EP3791874A4 (en) | 2018-05-08 | 2022-02-23 | National University Corporation Okayama University | USEFUL MEDICINES FOR CARDIOVASCULAR DISEASES |
| US20210299331A1 (en) | 2018-07-19 | 2021-09-30 | Kyoto University | Pluripotent stem cell-derived plate-shaped cartilage and method for producing the same |
| EP3900787A4 (en) | 2018-12-21 | 2022-02-23 | Kyoto University | Lubricin-localized cartilage-like tissue, method for producing same and composition comprising same for treating articular cartilage damage |
| EP3939656A4 (en) | 2019-03-13 | 2022-12-07 | National University Corporation Hamamatsu University School of Medicine | Pharmaceutical composition for treating aortic aneurysm |
| EP4108260A4 (en) | 2020-02-21 | 2024-03-06 | JSR Corporation | Composition for alleviating pulmonary hypertension, method for predicting prognosis of pulmonary hypertension, method for assisting in determining severity of pulmonary hypertension, and method for assisting in diagnosing pulmonary hypertension |
-
1980
- 1980-06-06 JP JP7612780A patent/JPS572240A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008102563A1 (ja) | 2007-02-23 | 2008-08-28 | Next21 K.K. | 血管攣縮の治療剤又は予防剤 |
| WO2010041619A1 (ja) | 2008-10-06 | 2010-04-15 | メルシャン株式会社 | シュードノカルディア・オートトロフィカ（Pseudonocardia autotrophica）発現ベクター |
| US9006412B2 (en) | 2008-10-06 | 2015-04-14 | Microbiopharm Japan Co., Ltd. | Expression vector for pseudonocardia autotrophica |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS572240A (en) | 1982-01-07 |
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