ATE328862T1 - Verfahren zur industriellen herstellung von betulinsäuren - Google Patents
Verfahren zur industriellen herstellung von betulinsäurenInfo
- Publication number
- ATE328862T1 ATE328862T1 AT01942354T AT01942354T ATE328862T1 AT E328862 T1 ATE328862 T1 AT E328862T1 AT 01942354 T AT01942354 T AT 01942354T AT 01942354 T AT01942354 T AT 01942354T AT E328862 T1 ATE328862 T1 AT E328862T1
- Authority
- AT
- Austria
- Prior art keywords
- betulin
- acetate
- dibenzoate
- betulinic
- industrial production
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 238000009776 industrial production Methods 0.000 title 1
- XUDTWJGGQFHXCR-VFUWXHBOSA-N [(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate Chemical compound C1C[C@H](OC(C)=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C XUDTWJGGQFHXCR-VFUWXHBOSA-N 0.000 abstract 10
- JYDNKGUBLIKNAM-UHFFFAOYSA-N Oxyallobutulin Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C JYDNKGUBLIKNAM-UHFFFAOYSA-N 0.000 abstract 7
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 abstract 7
- MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 abstract 7
- XUDTWJGGQFHXCR-UHFFFAOYSA-N betulinol acetate Natural products C1CC(OC(C)=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C XUDTWJGGQFHXCR-UHFFFAOYSA-N 0.000 abstract 5
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 abstract 2
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 abstract 2
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 abstract 2
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 abstract 2
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 abstract 2
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/480,406 US6232481B1 (en) | 2000-01-11 | 2000-01-11 | Method for manufacturing betulinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE328862T1 true ATE328862T1 (de) | 2006-06-15 |
Family
ID=23907841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT01942354T ATE328862T1 (de) | 2000-01-11 | 2001-01-11 | Verfahren zur industriellen herstellung von betulinsäuren |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6232481B1 (de) |
| EP (1) | EP1248766B1 (de) |
| JP (1) | JP2003519674A (de) |
| AT (1) | ATE328862T1 (de) |
| AU (1) | AU5789601A (de) |
| CA (1) | CA2396574A1 (de) |
| DE (1) | DE60120352T2 (de) |
| ES (1) | ES2264694T3 (de) |
| NO (1) | NO20023276L (de) |
| WO (1) | WO2001051451A2 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6232481B1 (en) * | 2000-01-11 | 2001-05-15 | Regents Of The University Of Minnesota | Method for manufacturing betulinic acid |
| US7407480B2 (en) * | 2001-07-27 | 2008-08-05 | Ams Research Corporation | Method and apparatus for correction of urinary and gynecological pathologies, including treatment of incontinence cystocele |
| RU2246500C1 (ru) * | 2003-06-24 | 2005-02-20 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Способ получения бетулиновой кислоты |
| EP1869063A2 (de) * | 2005-03-29 | 2007-12-26 | Regents Of The University Of Minnesota | Verfahren zur herstellung biologisch aktiver 3-ester von betulinaldehyd und betulinsäure |
| WO2006105354A1 (en) * | 2005-03-29 | 2006-10-05 | Regents Of The University Of Minnesota | Selective oxidation of triterpenes employing tempo |
| US20080308426A1 (en) * | 2005-03-29 | 2008-12-18 | Krasutsky Pavel A | Electrochemical Method for the Production of Betulin Aldehyde |
| US20090131714A1 (en) * | 2005-06-08 | 2009-05-21 | Krasutsky Pavel A | Synthesis of betulonic and betulinic aldehydes |
| CA2649704A1 (en) * | 2006-04-18 | 2007-10-25 | Regents Of The University Of Minnesota | Depolymerization extraction of compounds from birch bark |
| KR100941595B1 (ko) * | 2008-06-05 | 2010-02-11 | 주식회사 알앤엘바이오 | 바이러스 억제제로서 유용한 트리테르페노이드계 화합물 |
| CN101302244B (zh) * | 2008-06-06 | 2011-04-13 | 东北林业大学 | 一种桦木酸的生产方法 |
| CN102399255B (zh) * | 2010-09-09 | 2015-04-15 | 东北林业大学 | 一种桦木酸的制备方法 |
| RU2560710C1 (ru) * | 2014-10-30 | 2015-08-20 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) | Способ получения производных 3-ацетата-28-сульфата бетулина |
| PL227790B1 (pl) | 2015-08-13 | 2018-01-31 | Slaski Univ Medyczny W Katowicach | Fosfoniany acetylenowych pochodnych betuliny o działaniu przeciwnowotworowym, sposób ich wytwarzania i zastosowanie. |
| CN110577470B (zh) * | 2019-10-09 | 2022-12-27 | 蚌埠学院 | 一种利用沸石分子筛催化2-萘甲醚选择性硝化的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW212790B (de) | 1991-10-15 | 1993-09-11 | Ciba Geigy Ag | |
| US5804575A (en) | 1997-03-27 | 1998-09-08 | The Board Of Trustees Of The University Of Illinois | Methods of manufacturing betulinic acid |
| ES2281960T3 (es) * | 1998-03-02 | 2007-10-01 | The University Of North Carolina At Chapel Hill | Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso. |
| US6232481B1 (en) | 2000-01-11 | 2001-05-15 | Regents Of The University Of Minnesota | Method for manufacturing betulinic acid |
-
2000
- 2000-01-11 US US09/480,406 patent/US6232481B1/en not_active Expired - Lifetime
-
2001
- 2001-01-11 DE DE60120352T patent/DE60120352T2/de not_active Expired - Fee Related
- 2001-01-11 WO PCT/US2001/000991 patent/WO2001051451A2/en not_active Ceased
- 2001-01-11 EP EP01942354A patent/EP1248766B1/de not_active Expired - Lifetime
- 2001-01-11 JP JP2001551833A patent/JP2003519674A/ja not_active Withdrawn
- 2001-01-11 CA CA002396574A patent/CA2396574A1/en not_active Abandoned
- 2001-01-11 ES ES01942354T patent/ES2264694T3/es not_active Expired - Lifetime
- 2001-01-11 AT AT01942354T patent/ATE328862T1/de not_active IP Right Cessation
- 2001-01-11 AU AU57896/01A patent/AU5789601A/en not_active Abandoned
- 2001-01-16 US US09/761,351 patent/US6271405B2/en not_active Expired - Lifetime
- 2001-04-23 US US09/840,627 patent/US6867314B2/en not_active Expired - Lifetime
- 2001-06-29 US US09/896,803 patent/US6407270B1/en not_active Expired - Lifetime
-
2002
- 2002-07-05 NO NO20023276A patent/NO20023276L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6867314B2 (en) | 2005-03-15 |
| DE60120352T2 (de) | 2007-04-26 |
| NO20023276D0 (no) | 2002-07-05 |
| CA2396574A1 (en) | 2001-07-19 |
| EP1248766B1 (de) | 2006-06-07 |
| DE60120352D1 (de) | 2006-07-20 |
| NO20023276L (no) | 2002-09-09 |
| US20020028960A1 (en) | 2002-03-07 |
| AU5789601A (en) | 2001-07-24 |
| JP2003519674A (ja) | 2003-06-24 |
| ES2264694T3 (es) | 2007-01-16 |
| WO2001051451A2 (en) | 2001-07-19 |
| EP1248766A2 (de) | 2002-10-16 |
| US6407270B1 (en) | 2002-06-18 |
| US6271405B2 (en) | 2001-08-07 |
| US20010007908A1 (en) | 2001-07-12 |
| US20020016482A1 (en) | 2002-02-07 |
| WO2001051451A3 (en) | 2002-03-07 |
| US6232481B1 (en) | 2001-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification |
Ref document number: 1248766 Country of ref document: EP |
|
| REN | Ceased due to non-payment of the annual fee |