DE69633398D1 - Betulinsäure-derivate und ihre verwendungen - Google Patents
Betulinsäure-derivate und ihre verwendungenInfo
- Publication number
- DE69633398D1 DE69633398D1 DE69633398T DE69633398T DE69633398D1 DE 69633398 D1 DE69633398 D1 DE 69633398D1 DE 69633398 T DE69633398 T DE 69633398T DE 69633398 T DE69633398 T DE 69633398T DE 69633398 D1 DE69633398 D1 DE 69633398D1
- Authority
- DE
- Germany
- Prior art keywords
- betulinic acid
- acid derivatives
- substd
- opt
- dotted line
- 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
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class 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 2
- 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 1
- 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 1
- 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 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 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 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229930182480 glucuronide Natural products 0.000 abstract 1
- 150000008134 glucuronides Chemical class 0.000 abstract 1
- 239000003022 immunostimulating agent Substances 0.000 abstract 1
- 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 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 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
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/463,071 US5679828A (en) | 1995-06-05 | 1995-06-05 | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US463071 | 1995-06-05 | ||
| PCT/US1996/009485 WO1996039033A1 (en) | 1995-06-05 | 1996-06-05 | Betulinic acid derivatives and uses therefor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE69633398D1 true DE69633398D1 (de) | 2004-10-21 |
| DE69633398T2 DE69633398T2 (de) | 2005-09-22 |
| DE69633398T8 DE69633398T8 (de) | 2006-01-12 |
Family
ID=23838749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69633398T Active DE69633398T8 (de) | 1995-06-05 | 1996-06-05 | Betulinsäure-derivate und ihre verwendungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5679828A (de) |
| EP (2) | EP1397957A2 (de) |
| AT (1) | ATE275823T1 (de) |
| AU (1) | AU6328896A (de) |
| CA (1) | CA2223513C (de) |
| DE (1) | DE69633398T8 (de) |
| DK (1) | DK0857018T3 (de) |
| ES (1) | ES2231818T3 (de) |
| PT (1) | PT857018E (de) |
| WO (1) | WO1996039033A1 (de) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962527A (en) * | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| WO1998032443A1 (de) * | 1997-01-24 | 1998-07-30 | Marigen S.A. | Ultramikroemulsionen aus spontan dispergierbaren konzentraten enthaltend antitumoral, antiviral und antiparasitär wirksame ester von pentacyclischen triterpenen |
| US5750578A (en) * | 1997-02-11 | 1998-05-12 | Regents Of The University Of Minnesota | Use of betulin and analogs thereof to treat herpesvirus infection |
| DE69825446T2 (de) * | 1997-06-04 | 2005-09-29 | Cornell Research Foundation, Inc. | Betulinolderivate |
| US6048847A (en) * | 1997-09-30 | 2000-04-11 | Dabur Research Foundation | Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this |
| US6228850B1 (en) * | 1997-09-30 | 2001-05-08 | Dabur Research Foundation | Antiangiogenic activity of betulinic acid and its derivatives |
| US6670345B1 (en) * | 1997-09-30 | 2003-12-30 | Dabur Research Foundation | Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid |
| AU762404B2 (en) * | 1998-03-02 | 2003-06-26 | Panacos Pharmaceuticals, Inc. | Acylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US6303589B1 (en) * | 1998-12-08 | 2001-10-16 | Micro Flo Company | Pentacyclic triterpenes |
| US6369101B1 (en) | 1999-02-26 | 2002-04-09 | Regents Of The University Of Minnesota | Therapeutic method to treat herpes virus infection |
| US6392070B1 (en) * | 1999-08-10 | 2002-05-21 | Regents Of The University Of Minnesota | Birch bark processing and the isolation of natural products from birch bark |
| CN1152046C (zh) * | 1999-09-09 | 2004-06-02 | 达布尔研究基金会 | 新的桦木酸衍生物,该衍生物的制备方法及其在治疗与血管生成有关肿瘤中的应用 |
| CA2446748C (en) * | 2001-05-11 | 2011-03-08 | University Of Ottawa | Anxiolytic marcgraviaceae compositions containing betulinic acid, betulinic acid derivatives, and methods |
| US7365221B2 (en) * | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| EP1551790A4 (de) * | 2002-09-26 | 2009-10-21 | Panacos Pharmaceuticals Inc | Monoacylierte betulin- und dihydrobetulinderivate, deren herstellung und deren verwendung |
| US7537765B2 (en) * | 2003-01-29 | 2009-05-26 | Panacos Pharmaceuticals, Inc. | Inhibition of HIV-1 replication by disruption of the processing of the viral capsid-spacer peptide 1 protein |
| AU2004210162A1 (en) * | 2003-01-29 | 2004-08-19 | Panacos Pharmaceuticals, Inc. | Inhibition of HIV-1 replication by disruption of the processing of the viral capsid-spacer peptide 1 protein |
| US7026305B2 (en) * | 2003-04-14 | 2006-04-11 | Meharry Medical College | Anti-HIV agents with dual sites of action |
| CN100591688C (zh) * | 2004-03-17 | 2010-02-24 | 帕纳克斯医药公司 | 3-0-(3＇,3＇-二甲基琥珀酰基)桦木酸的药用盐 |
| RU2387665C2 (ru) * | 2004-03-17 | 2010-04-27 | Панакос Фармасьютикалз, Инк. | Фармацевтические соли 3-о-(3', 3'-диметилсукцинил)бетулиновой кислоты |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| MXPA06013698A (es) * | 2004-05-24 | 2007-08-15 | Panacos Pharmaceuticals Inc | Inhibicion de replicacion de virus 1 de inmunodeficiencia humana (vih-1) por interrupcion del procesamiento de la proteina de capsida-peptido separador 1 viral. |
| WO2006031756A2 (en) | 2004-09-10 | 2006-03-23 | Cornell Research Foundation, Inc | Betulinol derivatives as anti-cancer agents |
| TW200628161A (en) * | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| US7799768B2 (en) * | 2005-04-12 | 2010-09-21 | Myrexis, Inc. | Polymorphs of 3-O-(3′,3′-dimethylsuccinyl)betulinic acid di-N-methyl-D-glucamine |
| JP2008543945A (ja) * | 2005-06-22 | 2008-12-04 | ミリアド ジェネティクス， インコーポレイテッド | 抗ウイルス化合物 |
| BRPI0619936A2 (pt) * | 2005-12-16 | 2011-10-25 | Panacos Pharmaceuticals Inc | preparação de sais farmacêuticos de ácido 3-o-(3',3'- dimetilsuccinil) betulìnico |
| WO2007114978A2 (en) * | 2006-02-09 | 2007-10-11 | Boehringer Ingelheim International Gmbh | Method for treating hiv infection through co-administration of tipranavir and pa-457 |
| WO2007112043A2 (en) * | 2006-03-23 | 2007-10-04 | Advanced Life Sciences Inc. | Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin |
| US20080039428A1 (en) * | 2006-06-29 | 2008-02-14 | Panacos Pharmaceuticals, Inc. | Antiretroviral combination therapy |
| US20090105203A1 (en) * | 2006-10-16 | 2009-04-23 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| US9505800B2 (en) | 2006-11-03 | 2016-11-29 | Myrexis, Inc. | Extended triterpene derivatives |
| US20110152229A1 (en) * | 2006-11-22 | 2011-06-23 | Duke University | Betulinic acid derivatives as anti-hiv agents |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| HRP20150977T1 (hr) | 2010-06-04 | 2015-10-09 | Bristol-Myers Squibb Company | C-28 amidi modificiranih derivata c-3 betulinske kiseline kao inhibitori sazrijevanja hiv-a |
| JP5752789B2 (ja) * | 2010-06-04 | 2015-07-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体 |
| RU2448115C1 (ru) * | 2010-12-20 | 2012-04-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Новосибирский национальный исследовательский государственный университет" (Новосибирский государственный университет (НГУ) | Гидрированная бетулоновая кислота и ее амиды как противоопухолевые средства тритерпеновой природы |
| PE20141152A1 (es) | 2011-01-31 | 2014-09-22 | Bristol Myers Squibb Co | Triterpenoides c-17 y c-3 modificados con actividad inhibidora de la maduracion del virus de inmunodeficiencia humana |
| PL2670764T3 (pl) | 2011-01-31 | 2016-02-29 | Bristol Myers Squibb Co | C-28 aminy zmodyfikowanych C-3 pochodnych kwasu betulinowego jako inhibitory dojrzewania HIV |
| AU2012312485B2 (en) | 2011-09-21 | 2016-09-01 | VIIV Healthcare UK (No.5) Limited | Novel betulinic acid derivatives with antiviral activity |
| US8906889B2 (en) | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| CN103768078B (zh) | 2012-10-22 | 2019-02-05 | 北京大学 | 三萜衍生物及其抗流感用途 |
| US9637516B2 (en) | 2012-12-31 | 2017-05-02 | Hetero Research Foundation | Betulinic acid proline derivatives as HIV inhibitors |
| SG11201505639SA (en) | 2013-02-06 | 2015-08-28 | Bristol Myers Squibb Co | C-19 modified triterpenoids with hiv maturation inhibitory activity |
| US9249180B2 (en) | 2013-02-25 | 2016-02-02 | Bristol-Myers Squibb Company | C-3 alkyl and alkenyl modified betulinic acid derivatives |
| PL3129392T3 (pl) | 2014-04-11 | 2021-04-06 | VIIV Healthcare UK(No.4) Limited | Triterpenoidy o aktywności hamującej dojrzewanie hiv, podstawione w pozycji 3 niearomatycznym pierścieniem zawierającym podstawnik fluorowcoalkilowy |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
| US10047118B2 (en) | 2014-11-14 | 2018-08-14 | VIIV Healthcare UK (No.5) Limited | C17-aryl substituted betulinic acid analogs |
| KR20170087478A (ko) | 2014-11-14 | 2017-07-28 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 옥소루펜 유도체 |
| MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
| US10370405B2 (en) | 2015-03-16 | 2019-08-06 | Hetero Labs Limited | C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors |
| 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. |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| US20220296610A1 (en) * | 2017-04-06 | 2022-09-22 | Derm-Biome Pharmaceuticals Inc. | Compositions and methods for treatment of infection and novel cosmeceutical preparations |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US11236122B2 (en) | 2018-06-29 | 2022-02-01 | Dfh Therapeutics | Triterpene amine derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1415601A (en) * | 1973-03-14 | 1975-11-26 | Biorex Laboratories Ltd | Dihydrobetulinic acid derivatives |
| FR2683531B1 (fr) * | 1991-11-13 | 1993-12-31 | Rhone Poulenc Rorer Sa | Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| US5643884A (en) * | 1993-08-09 | 1997-07-01 | Glycomed Incorporated | Lupane triterpenoid derivatives |
-
1995
- 1995-06-05 US US08/463,071 patent/US5679828A/en not_active Expired - Lifetime
-
1996
- 1996-06-05 ES ES96922408T patent/ES2231818T3/es not_active Expired - Lifetime
- 1996-06-05 EP EP20030027166 patent/EP1397957A2/de not_active Withdrawn
- 1996-06-05 EP EP96922408A patent/EP0857018B1/de not_active Expired - Lifetime
- 1996-06-05 CA CA002223513A patent/CA2223513C/en not_active Expired - Fee Related
- 1996-06-05 WO PCT/US1996/009485 patent/WO1996039033A1/en active Search and Examination
- 1996-06-05 DK DK96922408T patent/DK0857018T3/da active
- 1996-06-05 AT AT96922408T patent/ATE275823T1/de not_active IP Right Cessation
- 1996-06-05 PT PT96922408T patent/PT857018E/pt unknown
- 1996-06-05 DE DE69633398T patent/DE69633398T8/de active Active
- 1996-06-05 AU AU63288/96A patent/AU6328896A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1397957A2 (de) | 2004-03-17 |
| PT857018E (pt) | 2005-01-31 |
| DK0857018T3 (da) | 2004-11-29 |
| ES2231818T3 (es) | 2005-05-16 |
| EP0857018B1 (de) | 2004-09-15 |
| EP0857018A1 (de) | 1998-08-12 |
| ATE275823T1 (de) | 2004-10-15 |
| DE69633398T2 (de) | 2005-09-22 |
| WO1996039033A1 (en) | 1996-12-12 |
| CA2223513C (en) | 2009-03-24 |
| US5679828A (en) | 1997-10-21 |
| EP0857018A4 (de) | 2002-10-23 |
| DE69633398T8 (de) | 2006-01-12 |
| CA2223513A1 (en) | 1996-12-12 |
| AU6328896A (en) | 1996-12-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL, CHAPE Owner name: PANACOS PHARMACEUTICALS, INC., GAITHERSBURG, MD., |
|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL, C, US Owner name: PANACOS PHARMACEUTICALS, INC., GAITHERSBURG, M, US |