JPH0556332B2 - - Google Patents
Info
- Publication number
- JPH0556332B2 JPH0556332B2 JP26947384A JP26947384A JPH0556332B2 JP H0556332 B2 JPH0556332 B2 JP H0556332B2 JP 26947384 A JP26947384 A JP 26947384A JP 26947384 A JP26947384 A JP 26947384A JP H0556332 B2 JPH0556332 B2 JP H0556332B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- oxo
- reaction
- hydroxy
- 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 - Lifetime
Links
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical class C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 24
- 239000002253 acid Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 5
- 229960003720 enoxolone Drugs 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- -1 lactone derivative of glycyrrhetinic acid Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000007248 oxidative elimination reaction Methods 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011218 seed culture Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000187090 Streptomyces sclerotialus Species 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26947384A JPS61148142A (ja) | 1984-12-20 | 1984-12-20 | グリチルレチン酸セコ型誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26947384A JPS61148142A (ja) | 1984-12-20 | 1984-12-20 | グリチルレチン酸セコ型誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61148142A JPS61148142A (ja) | 1986-07-05 |
| JPH0556332B2 true JPH0556332B2 (enrdf_load_stackoverflow) | 1993-08-19 |
Family
ID=17472926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26947384A Granted JPS61148142A (ja) | 1984-12-20 | 1984-12-20 | グリチルレチン酸セコ型誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61148142A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5519008A (en) * | 1992-09-10 | 1996-05-21 | Glycomed Incorporated | Derivatives of triterpenoid acids as inhibitors of cell-adhesion molecules ELAM-1 (E-selectin) and LECAM-1 (L-selectin) |
| CN112608800A (zh) * | 2020-12-17 | 2021-04-06 | 江苏耐雀生物工程技术有限公司 | 一种具有抗敏功能的手工皂及其制备方法 |
-
1984
- 1984-12-20 JP JP26947384A patent/JPS61148142A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61148142A (ja) | 1986-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4399282A (en) | Camptothecin derivatives | |
| US11384116B2 (en) | Methods of making cholic acid derivatives and starting materials therefor | |
| JPH09510966A (ja) | シクロヘキシルアゼチジノンの製造法 | |
| JPH0710876B2 (ja) | マクロライド誘導体の改良製造法 | |
| HU198938B (en) | Process for producing podophyllotoxin and podophyllotoxin derivatives | |
| EP0418925B1 (en) | Method of producing (S)-4-hydroxymethyl-gamma-lactone | |
| AU771214B2 (en) | Process for the isolation of pseudomonic acid a from pseudomonic acid complex-containing culture broth | |
| FR2473519A1 (fr) | Terpenoides contenant deux groupes fonctionnels, leur preparation et leur application therapeutique | |
| JPH0556332B2 (enrdf_load_stackoverflow) | ||
| SU860708A1 (ru) | Способ получени стероидов | |
| JPH058179B2 (enrdf_load_stackoverflow) | ||
| US4528372A (en) | N-Phthalidyl-5-fluorouracils | |
| JPH06256278A (ja) | 光学活性α−カルバモイルアルカン酸誘導体およびその製法 | |
| US6051721A (en) | Ring E-modified analogues of(-)-podophyllotoxin and etoposide and a method for their synthesis | |
| EP0469480A2 (de) | Verfahren zur stereoselektiven Herstellung von 5-substituierten delta-Lactonen und deren Verwendung | |
| US4158061A (en) | 2,9-Dioxatricyclo[4,3,1,03,7 ] decane derivatives, processes for their preparation and pharmaceutical compositions thereof | |
| JPH0362718B2 (enrdf_load_stackoverflow) | ||
| WO1996006829A1 (fr) | Derive de 1,4-dihydropyrydine | |
| JPS6258351B2 (enrdf_load_stackoverflow) | ||
| JP2700818B2 (ja) | エキソ型３’，４’―ｏ―ベンジリデン―３”―デメチルチャートルシン及びその塩 | |
| JP2001523259A (ja) | ４−アザ−ステロイド類 | |
| US2694068A (en) | Ag-desoxymorphine compounds and proc- | |
| JPH0362717B2 (enrdf_load_stackoverflow) | ||
| US4188329A (en) | Intermediates for the preparation of prostaglandins and prostaglandin analogs from a mold metabolite | |
| JP2675569B2 (ja) | ２，３−ジヒドロベンゾフラン誘導体の製造方法 |