CA1208625A - Pharmaceutically active ursolic acid derivatives - Google Patents
Pharmaceutically active ursolic acid derivativesInfo
- Publication number
- CA1208625A CA1208625A CA000432961A CA432961A CA1208625A CA 1208625 A CA1208625 A CA 1208625A CA 000432961 A CA000432961 A CA 000432961A CA 432961 A CA432961 A CA 432961A CA 1208625 A CA1208625 A CA 1208625A
- Authority
- CA
- Canada
- Prior art keywords
- ursa
- dien
- beta
- acid
- oic acid
- 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
- 150000003675 ursolic acids Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 230000000767 anti-ulcer Effects 0.000 abstract description 6
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 230000003902 lesion Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].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](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 description 5
- 229960000530 carbenoxolone Drugs 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000002395 mineralocorticoid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 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 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010061218 Inflammation Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010041277 Sodium retention Diseases 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 210000002249 digestive system Anatomy 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Substances BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229960003720 enoxolone Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005048 flame photometry Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 1
- 230000035322 succinylation Effects 0.000 description 1
- 238000010613 succinylation reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8222566A IT1215626B (it) | 1982-07-26 | 1982-07-26 | Derivato dell'acido ursolico farmacologicamente attivo. |
| IT22566A/82 | 1982-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1208625A true CA1208625A (en) | 1986-07-29 |
Family
ID=11197905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000432961A Expired CA1208625A (en) | 1982-07-26 | 1983-07-22 | Pharmaceutically active ursolic acid derivatives |
Country Status (11)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183007U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1984-11-06 | 1986-06-02 | ||
| JPH07583B2 (ja) * | 1990-11-21 | 1995-01-11 | 北海道糖業株式会社 | 水溶性五環性トリテルペン包接化合物及びその製造方法並びにそれを利用した食品、飲料、口腔用組成物 |
| GB9110929D0 (en) * | 1991-05-21 | 1991-07-10 | Idb Holding Spa | Ursane derivatives,their preparation and pharmaceutical formulations thereof |
| US6982284B1 (en) | 1999-09-10 | 2006-01-03 | Applied Genetics Incorporated Dermatics | Compositions and methods for modification of skin lipid content |
| AU2001283038A1 (en) * | 2000-07-31 | 2002-02-13 | University Of Virginia Patent Foundation | Inhibitors of dna polymerase sigma |
| US20040029906A1 (en) * | 2001-07-31 | 2004-02-12 | Michael Christman | Inhibitors of dna polymerase sigma |
| CN102241723B (zh) * | 2010-05-11 | 2015-06-03 | 上海开拓者医药发展有限公司 | 一种熊果酸盐及其制备方法和晶体 |
| KR101889528B1 (ko) | 2012-08-14 | 2018-08-17 | 넥스올리고(주) | 신규한 우르솔릭산 유도체 및 이의 제조 방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1076684B (de) * | 1957-07-16 | 1960-03-03 | Biorex Laboratories Ltd | Verfahren zur Herstellung von pharmakologisch wirksamen Verbindungen der Glycyrrhetinsaeure |
| GB1138247A (en) * | 1966-08-26 | 1968-12-27 | Biorex Laboratories Ltd | Oleanolic acid derivatives |
| IT1051001B (it) * | 1971-08-06 | 1981-04-21 | Isf Spa | Processo per la preparazione dell acido 3 o beta carbossipropionil ibbeta glicirretico |
| GB1414047A (en) * | 1973-03-15 | 1975-11-12 | Biorex Laboratories Ltd | Ursolic acid derivatives |
| GB1435622A (en) * | 1973-11-07 | 1976-05-12 | Biorex Laboratories Ltd | Erythrodiol derivatives |
| GB1475075A (en) * | 1974-09-11 | 1977-06-01 | Biorex Laboratories Ltd | Derivatives of glycyrrhetinic and oleanolic acids |
| GB1476053A (en) * | 1975-02-07 | 1977-06-10 | Biorex Laboratories Ltd | Glycyrrhetinic acid derivatives |
| JPS588044A (ja) * | 1981-07-06 | 1983-01-18 | Maruzen Seiyaku Kk | １１−デオキソグリチルレチン酸水素マレ−ト及びそれを有効成分とする医薬 |
-
1982
- 1982-07-26 IT IT8222566A patent/IT1215626B/it active
-
1983
- 1983-07-22 PT PT77083A patent/PT77083B/pt not_active IP Right Cessation
- 1983-07-22 CA CA000432961A patent/CA1208625A/en not_active Expired
- 1983-07-23 ES ES524408A patent/ES524408A0/es active Granted
- 1983-07-25 DK DK339783A patent/DK339783A/da not_active Application Discontinuation
- 1983-07-25 AU AU17261/83A patent/AU552998B2/en not_active Ceased
- 1983-07-25 US US06/511,761 patent/US4530934A/en not_active Expired - Fee Related
- 1983-07-25 JP JP58134520A patent/JPS5933243A/ja active Granted
- 1983-07-26 DE DE8383107337T patent/DE3374059D1/de not_active Expired
- 1983-07-26 AT AT83107337T patent/ATE30231T1/de not_active IP Right Cessation
- 1983-07-26 EP EP83107337A patent/EP0100516B1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0373533B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-11-22 |
| ES8502076A1 (es) | 1984-12-16 |
| ATE30231T1 (de) | 1987-10-15 |
| EP0100516A3 (en) | 1985-11-06 |
| DK339783A (da) | 1984-01-27 |
| ES524408A0 (es) | 1984-12-16 |
| IT1215626B (it) | 1990-02-22 |
| PT77083A (en) | 1983-08-01 |
| DK339783D0 (da) | 1983-07-25 |
| JPS5933243A (ja) | 1984-02-23 |
| EP0100516B1 (de) | 1987-10-14 |
| US4530934A (en) | 1985-07-23 |
| DE3374059D1 (en) | 1987-11-19 |
| AU1726183A (en) | 1984-02-02 |
| AU552998B2 (en) | 1986-06-26 |
| EP0100516A2 (de) | 1984-02-15 |
| PT77083B (en) | 1986-04-11 |
| IT8222566A0 (it) | 1982-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |