RU2065864C1 - Производные глицирретовой кислоты и способ их получения - Google Patents
Производные глицирретовой кислоты и способ их получения Download PDFInfo
- Publication number
- RU2065864C1 RU2065864C1 SU925011293A SU5011293A RU2065864C1 RU 2065864 C1 RU2065864 C1 RU 2065864C1 SU 925011293 A SU925011293 A SU 925011293A SU 5011293 A SU5011293 A SU 5011293A RU 2065864 C1 RU2065864 C1 RU 2065864C1
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- Prior art keywords
- acid
- phosphoryl
- ascorbyl
- compound according
- compound
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000002253 acid Substances 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title description 8
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- 239000000203 mixture Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 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 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
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- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- RMIVRCBSQPCSCQ-BDANYOJNSA-N methyl (2s,4as,6ar,6as,6br,8ar,10s,12as,14br)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1h-picene-2-carboxylate Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@](C(=O)OC)(C)C[C@H]5C4=CC(=O)[C@@H]3[C@]21C RMIVRCBSQPCSCQ-BDANYOJNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3128799A JP2998287B2 (ja) | 1991-03-13 | 1991-03-13 | グリチルレチン酸誘導体 |
| JP128799-91 | 1991-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2065864C1 true RU2065864C1 (ru) | 1996-08-27 |
Family
ID=14993725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU925011293A RU2065864C1 (ru) | 1991-03-13 | 1992-03-12 | Производные глицирретовой кислоты и способ их получения |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5229378A (OSRAM) |
| EP (1) | EP0503582B1 (OSRAM) |
| JP (1) | JP2998287B2 (OSRAM) |
| KR (1) | KR0185717B1 (OSRAM) |
| AT (1) | ATE161848T1 (OSRAM) |
| CA (1) | CA2062652A1 (OSRAM) |
| DE (1) | DE69223827T2 (OSRAM) |
| ES (1) | ES2112870T3 (OSRAM) |
| RU (1) | RU2065864C1 (OSRAM) |
| TW (1) | TW201750B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2611362C1 (ru) * | 2015-11-26 | 2017-02-21 | Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН) | Водорастворимая композиция, обладающая противоопухолевой активностью и способ ее получения |
| RU2623876C2 (ru) * | 2014-11-10 | 2017-06-29 | Александр Владимирович Диковский | Фармацевтическая композиция для лечения гиперлипидемии |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1254321B (it) * | 1992-04-10 | 1995-09-14 | Kemiprogress S R L | Composizione farmaceutica per il trattamento e la prevenzione delle infiammazioni cutanee e della mucosa orale. |
| 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) |
| US5527890A (en) * | 1993-04-16 | 1996-06-18 | Glycomed Incorporated | Derivatives of triterpenoid acids and uses thereof |
| CN1034334C (zh) * | 1993-08-14 | 1997-03-26 | 贵州省中医研究所 | 齐酞酸钠及其药物组合物 |
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| CA2244535A1 (en) * | 1995-05-15 | 2000-01-30 | Avon Products, Inc. | Novel uses for ascorbyl-phosphoryl-cholesterol in topical compositions |
| US5866147A (en) * | 1995-05-15 | 1999-02-02 | Avon Products, Inc. | Ascorbyl-phosphoryl-cholesterol |
| US5607968A (en) * | 1995-06-07 | 1997-03-04 | Avon Products, Inc. | Topical alkyl-2-O-L-ascorbyl-phosphates |
| DE69605556T2 (de) * | 1996-05-14 | 2000-06-15 | Avon Products, Inc. | Ascorbyl-phosphorylcholesterol |
| US7151082B2 (en) * | 1999-02-11 | 2006-12-19 | The Feinstein Institute For Medical Research | Antagonists of HMG1 for treating inflammatory conditions |
| US6303321B1 (en) | 1999-02-11 | 2001-10-16 | North Shore-Long Island Jewish Research Institute | Methods for diagnosing sepsis |
| EP1360965A4 (en) | 2001-02-16 | 2009-07-29 | Asubio Pharma Co Ltd | METHOD FOR THE TREATMENT OF DISEASES ASSOCIATED WITH A DECREASE OF THE EXPOSURE OF THE AOP-1 GENE OR AOP-1 AND MEANS FOR THE TREATMENT OF THE DISEASES |
| US7304034B2 (en) * | 2001-05-15 | 2007-12-04 | The Feinstein Institute For Medical Research | Use of HMGB fragments as anti-inflammatory agents |
| US7696169B2 (en) * | 2003-06-06 | 2010-04-13 | The Feinstein Institute For Medical Research | Inhibitors of the interaction between HMGB polypeptides and toll-like receptor 2 as anti-inflammatory agents |
| AU2004272607B2 (en) * | 2003-09-11 | 2008-11-06 | Cornerstone Therapeutics Inc. | Monoclonal antibodies against HMGB1 |
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| CN115813859B (zh) * | 2022-12-13 | 2024-05-17 | 五邑大学 | 一种甘草次酸配体脂质体及其制备方法和应用 |
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| IL24113A (en) * | 1965-08-08 | 1969-06-25 | Greidinger D | Glycyrrhetic acid phosphoric acid ester and salts thereof |
| GB1093908A (en) * | 1965-11-26 | 1967-12-06 | Biorex Laboratories Ltd | New derivatives of glycyrrhetinic acid |
| GB1229562A (OSRAM) * | 1969-01-17 | 1971-04-28 | ||
| US3734944A (en) * | 1970-05-15 | 1973-05-22 | Biorex Laboratories Ltd | Glycyrrhetinic acid esters |
| GB1476053A (en) * | 1975-02-07 | 1977-06-10 | Biorex Laboratories Ltd | Glycyrrhetinic acid derivatives |
| US4939128A (en) * | 1988-04-25 | 1990-07-03 | Takeda Chemical Industries, Ltd. | Ester of ascorbic acid 2-phosphate and pharmaceutical use |
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-
1992
- 1992-03-10 US US07/849,574 patent/US5229378A/en not_active Expired - Fee Related
- 1992-03-10 TW TW081101804A patent/TW201750B/zh active
- 1992-03-11 DE DE69223827T patent/DE69223827T2/de not_active Expired - Fee Related
- 1992-03-11 AT AT92104149T patent/ATE161848T1/de not_active IP Right Cessation
- 1992-03-11 EP EP92104149A patent/EP0503582B1/en not_active Expired - Lifetime
- 1992-03-11 CA CA002062652A patent/CA2062652A1/en not_active Abandoned
- 1992-03-11 ES ES92104149T patent/ES2112870T3/es not_active Expired - Lifetime
- 1992-03-12 RU SU925011293A patent/RU2065864C1/ru active
- 1992-03-13 KR KR1019920004158A patent/KR0185717B1/ko not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
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| 1. Химический фармацевтический журнал, 1988, 22, N 6, с.694-697. 2.Патент СССР N 1190989, кл. C 07 J 63/00, 1985. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2623876C2 (ru) * | 2014-11-10 | 2017-06-29 | Александр Владимирович Диковский | Фармацевтическая композиция для лечения гиперлипидемии |
| RU2611362C1 (ru) * | 2015-11-26 | 2017-02-21 | Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН) | Водорастворимая композиция, обладающая противоопухолевой активностью и способ ее получения |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE161848T1 (de) | 1998-01-15 |
| CA2062652A1 (en) | 1992-09-14 |
| TW201750B (OSRAM) | 1993-03-11 |
| JPH04330088A (ja) | 1992-11-18 |
| EP0503582A1 (en) | 1992-09-16 |
| KR920018062A (ko) | 1992-10-21 |
| JP2998287B2 (ja) | 2000-01-11 |
| EP0503582B1 (en) | 1998-01-07 |
| ES2112870T3 (es) | 1998-04-16 |
| KR0185717B1 (ko) | 1999-05-15 |
| DE69223827T2 (de) | 1998-06-18 |
| DE69223827D1 (de) | 1998-02-12 |
| US5229378A (en) | 1993-07-20 |
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