NO20023276L - Fremgangsmåter fremstilling av betulinsyre - Google Patents

Fremgangsmåter fremstilling av betulinsyre

Info

Publication number: NO20023276L
Authority: NO; Norway
Prior art keywords: betulin; acetate; betulinic acid; dibenzoate; betulinic
Prior art date: 2000-01-11

Application number

NO20023276A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023276D0 (no

Inventor

Pavel A Krasutsky

Robert M Carlson

Vitaliy V Nesterenko

Original Assignee

Univ Minnesota

Priority date (The priority date 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 date listed.)

2000-01-11

Filing date

2002-07-05

Publication date

2002-09-09

2002-07-05 Application filed by Univ Minnesota filed Critical Univ Minnesota

2002-07-05 Publication of NO20023276D0 publication Critical patent/NO20023276D0/no

2002-09-09 Publication of NO20023276L publication Critical patent/NO20023276L/no

Links

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 title abstract 3
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 title abstract 3
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 title abstract 3
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 title abstract 3
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 title abstract 3
238000000034 method Methods 0.000 title abstract 3
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 title abstract 3
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
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)

NO20023276A 2000-01-11 2002-07-05 Fremgangsmåter fremstilling av betulinsyre NO20023276L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/480,406 US6232481B1 (en)	2000-01-11	2000-01-11	Method for manufacturing betulinic acid
PCT/US2001/000991 WO2001051451A2 (en)	2000-01-11	2001-01-11	Methods for manufacturing betulinic acid

Publications (2)

Publication Number	Publication Date
NO20023276D0 NO20023276D0 (no)	2002-07-05
NO20023276L true NO20023276L (no)	2002-09-09

Family

ID=23907841

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20023276A NO20023276L (no)	2000-01-11	2002-07-05	Fremgangsmåter fremstilling av betulinsyre

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)

* Cited by examiner, † Cited by third party
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
US20090076290A1 (en) *	2005-03-29	2009-03-19	Regents Of The University Of Minnesota	Selective oxidation of triterpenes employing tempo
WO2006105356A2 (en) *	2005-03-29	2006-10-05	Regents Of The University Of Minnesota	Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid
WO2006105357A2 (en) *	2005-03-29	2006-10-05	Regents Of The University Of Minnesota	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
WO2007121482A1 (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)

* Cited by examiner, † Cited by third party
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
ATE348839T1 (de) *	1998-03-02	2007-01-15	Univ North Carolina	Acylierte betulin- und dihydrobetulinderivate, ihre herstellung und verwendung
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 AU AU57896/01A patent/AU5789601A/en not_active Abandoned
- 2001-01-11 CA CA002396574A patent/CA2396574A1/en not_active Abandoned
- 2001-01-11 WO PCT/US2001/000991 patent/WO2001051451A2/en not_active Ceased
- 2001-01-11 DE DE60120352T patent/DE60120352T2/de not_active Expired - Fee Related
- 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 ES ES01942354T patent/ES2264694T3/es not_active Expired - Lifetime
- 2001-01-11 AT AT01942354T patent/ATE328862T1/de not_active IP Right Cessation
- 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
US6407270B1 (en)	2002-06-18
US6271405B2 (en)	2001-08-07
EP1248766B1 (de)	2006-06-07
AU5789601A (en)	2001-07-24
DE60120352D1 (de)	2006-07-20
ES2264694T3 (es)	2007-01-16
US20020028960A1 (en)	2002-03-07
EP1248766A2 (de)	2002-10-16
ATE328862T1 (de)	2006-06-15
WO2001051451A2 (en)	2001-07-19
JP2003519674A (ja)	2003-06-24
US20010007908A1 (en)	2001-07-12
US6232481B1 (en)	2001-05-15
US20020016482A1 (en)	2002-02-07
WO2001051451A3 (en)	2002-03-07

Publication	Publication Date	Title
NO20023276D0 (no)	2002-07-05	Fremgangsmåte til å fremstille betulinsyre
IT1317034B1 (it)	2003-05-26	Metodo di estrazione di prodotti ad attivita' farmaceutica da piantespermatofite, prodotti cosi' ottenuti e loro impiego in medicina, in
NO20020651D0 (no)	2002-02-08	Björkebarkbehandling og isolering av naturprodukter fra björkebark
ES2189768T3 (es)	2003-07-16	Sintesis regioselectiva de derivados de rapamicina.
DK1257531T3 (da)	2005-01-17	Fremgangsmåde til fremstilling af carbothiosyre
IL140419A0 (en)	2002-02-10	Novel form of irbesartan, methods for obtaining said form and pharmaceutical compositions containing same
ATE250077T1 (de)	2003-10-15	Steroid sulfataseinhibitoren, verfahren zu ihrer herstellung und verwendung
DK1301526T3 (da)	2008-10-06	Fremgangsmåde til oxidation til fremstilling af mellemproduktet 6.alpha.,9alpha.-difluor-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-androst-1,4-dien-3-on 17.beta-carboxylsyre
AU2001263300A1 (en)	2001-12-03	Post-added alpha-sulfofatty acid ester compositions and methods of making and using the same
DK32684A (da)	1984-01-25	Fremgangsmaade til fremstilling af 26,26,26,27,27,27-hexafluor-1alfa,25-dihydroxycholesterol og mellemprodukter til brug herfor
IS7365A (is)	2004-07-22	Hvarfgjörn þynningarefni og húðir sem innihalda þau
DE60322852D1 (de)	2008-09-25	Verfahren zur herstellung von eplerenon
DE50107209D1 (de)	2005-09-29	Verfahren zur herstellung von 5-aminosalicylsäure
NO20022361L (no)	2002-07-10	Fremgangsmåte for fremstilling av konjugert linolsyre
ATE212019T1 (de)	2002-02-15	Verfahren zur herstellung von phenylheterocyclen die als cox-2 inhibitoren verwendet werden können
DE60003807D1 (de)	2003-08-14	Enantiomere von mercaptolactonen und verfahren zu ihrer herstellung
DK1322660T3 (da)	2007-01-08	17a-fluoralkylsteroider, fremgangsmåde til deres fremstilling og farmaceutiske sammensætninger, der indeholder disse forbindelser
HU0102118D0 (en)	2001-07-30	Process for chloromethylation
PL338215A1 (en)	2000-10-09	Method of obtaining 3-cyano-2,4-dichlorogeno-5-fluorobenzoic acids
DK1196428T3 (da)	2005-01-24	11-beta-aryl-17,17-spirothiolan-substituerede steroider
DE60014103D1 (de)	2004-10-28	Verfahren zur herstellung von debromohymenialdisin und deren analogen
ES2194529T3 (es)	2003-11-16	Procedimiento de preparacion de un agente plastificante de alta energia.
DK1163257T3 (da)	2003-03-03	Fremgangsmåde til fremstilling af 4,4-dimethyl-3beta-hydroxypregna-8,14-dien-21-carboxylsyreestere og mellemprodukter i fremgangsmåden
DK0866798T3 (da)	2003-09-01	Fremstilling af esterderivater af steroider
AU5650590A (en)	1991-01-07	Oxidative preparation of a-nor-17 beta-carboxy-3,5-secoandrostan-5-one-3 oic acid