TWI628188B - 具有ｈｉｖ成熟抑制活性之ｃ－１７及ｃ－３經修飾之三萜類化合物 - Google Patents
具有ｈｉｖ成熟抑制活性之ｃ－１７及ｃ－３經修飾之三萜類化合物 Download PDFInfo
- Publication number
- TWI628188B TWI628188B TW101103140A TW101103140A TWI628188B TW I628188 B TWI628188 B TW I628188B TW 101103140 A TW101103140 A TW 101103140A TW 101103140 A TW101103140 A TW 101103140A TW I628188 B TWI628188 B TW I628188B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- group
- substituted
- compound
- pentamethyl
- Prior art date
Links
- 0 CC(C)([C@]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@](C)(CC(*2CC3)NC(N4CCNCC4)=O)[C@]1[C@@]2[C@@]3C(C)=C Chemical compound CC(C)([C@]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@](C)(CC(*2CC3)NC(N4CCNCC4)=O)[C@]1[C@@]2[C@@]3C(C)=C 0.000 description 2
- GRZUCBZTNBUFHX-NLVCBXEWSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CCC1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NC(N(C)/C=C/N1CCCC1)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CCC1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NC(N(C)/C=C/N1CCCC1)=O GRZUCBZTNBUFHX-NLVCBXEWSA-N 0.000 description 1
- JIOAHOPLIAMQBP-PQBBHEMQSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NC(N(C)CCCN(C)C)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3C(O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NC(N(C)CCCN(C)C)=O JIOAHOPLIAMQBP-PQBBHEMQSA-N 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- 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
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437893P | 2011-01-31 | 2011-01-31 | |
| US61/437,893 | 2011-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201309717A TW201309717A (zh) | 2013-03-01 |
| TWI628188B true TWI628188B (zh) | 2018-07-01 |
Family
ID=45567147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101103140A TWI628188B (zh) | 2011-01-31 | 2012-01-31 | 具有ｈｉｖ成熟抑制活性之ｃ－１７及ｃ－３經修飾之三萜類化合物 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US8846647B2 (enExample) |
| EP (1) | EP2670765B1 (enExample) |
| JP (1) | JP6001560B2 (enExample) |
| KR (1) | KR101886467B1 (enExample) |
| CN (1) | CN103429607B (enExample) |
| AR (1) | AR085053A1 (enExample) |
| AU (1) | AU2012212509B2 (enExample) |
| BR (1) | BR112013019419A2 (enExample) |
| CA (1) | CA2826113C (enExample) |
| CL (1) | CL2013002185A1 (enExample) |
| CO (1) | CO6751275A2 (enExample) |
| EA (1) | EA022470B1 (enExample) |
| ES (1) | ES2653847T3 (enExample) |
| IL (1) | IL227678B (enExample) |
| MA (1) | MA34909B1 (enExample) |
| MY (1) | MY162186A (enExample) |
| PE (1) | PE20141152A1 (enExample) |
| PH (1) | PH12013501528A1 (enExample) |
| PT (1) | PT2670765T (enExample) |
| SG (1) | SG192144A1 (enExample) |
| TN (1) | TN2013000321A1 (enExample) |
| TW (1) | TWI628188B (enExample) |
| UY (1) | UY33886A (enExample) |
| WO (1) | WO2012106190A1 (enExample) |
| ZA (1) | ZA201306546B (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104250280A (zh) | 2008-04-18 | 2014-12-31 | 里亚塔医药公司 | 抗氧化剂炎症调节剂:c-17同系化齐墩果酸衍生物 |
| KR101713140B1 (ko) | 2008-04-18 | 2017-03-08 | 리타 파마슈티컬스 잉크. | Ｃ-환에서 포화된 산화방지성 염증 조절제 올레아놀산 유도체 |
| MX339476B (es) | 2008-04-18 | 2016-05-27 | Reata Pharmaceuticals Inc | Compuestos que incluyen un nucleo farmaceutico antiinflamatorio y sus metodos de uso. |
| ES2703274T3 (es) | 2008-04-18 | 2019-03-07 | Reata Pharmaceuticals Inc | Moduladores de la inflamación antioxidantes: derivados del ácido oleanólico con modificaciones amino y otras en C-17 |
| HRP20171859T1 (hr) | 2010-12-17 | 2018-01-26 | Reata Pharmaceuticals, Inc. | Pirazolil i pirimidinil triciklički enoni kao antioksidacijski modulatori upale |
| HRP20151212T1 (hr) * | 2011-01-31 | 2015-12-04 | Bristol-Myers Squibb Company | C-28 AMINI C-3 MODIFICIRANIH DERIVATA BETULINSKE KISELINE KAO INHIBITORI SAZRIJEVANJA HIV-a P |
| CA2829618C (en) | 2011-03-11 | 2019-07-09 | Reata Pharmaceuticals, Inc. | C4-monomethyl triterpenoid derivatives and methods of use thereof |
| CA2849475A1 (en) | 2011-09-21 | 2013-03-28 | Bristol-Myers Squibb Company | 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 |
| DK3444261T3 (da) | 2012-04-27 | 2021-03-08 | Reata Pharmaceuticals Inc | 2,2-difluorpropionamidderivat af bardoxolonmethyl, farmaceutiske sammensætninger og polymorfer deraf til anvendelse ved behandling af visse lidelser |
| US8889854B2 (en) * | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| US9556222B2 (en) | 2012-06-15 | 2017-01-31 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| WO2014027045A1 (en) * | 2012-08-15 | 2014-02-20 | Glaxo Group Limited | Chemical process |
| PL2892912T3 (pl) | 2012-09-10 | 2019-10-31 | Reata Pharmaceuticals Inc | C17-alkanodiylowe i alkenodiylowe pochodne kwasu oleanolowego i sposoby ich zastosowania |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
| EA027371B1 (ru) * | 2013-02-06 | 2017-07-31 | Бристол-Майерс Сквибб Компани | C-19 модифицированные тритерпеноиды с ингибиторной активностью созревания вич |
| JP6186012B2 (ja) | 2013-02-25 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ−３アルキルおよびアルケニル修飾ベツリン酸誘導体 |
| NZ724644A (en) | 2014-04-11 | 2023-07-28 | Viiv Healthcare Uk No 4 Ltd | Triterpenoids with hiv maturation inhibitory activity, substituted in position 3 by a non-aromatic ring carrying a haloalkyl substituent |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| EP3218387A1 (en) | 2014-11-14 | 2017-09-20 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| BR112017009852A2 (pt) | 2014-11-14 | 2018-01-16 | Viiv Healthcare Uk No 5 Ltd | composto, composição, e, usos de um composto |
| CN107428798A (zh) * | 2015-04-14 | 2017-12-01 | Viiv保健英国第四有限公司 | 生产hiv成熟抑制剂的方法 |
| KR20180028534A (ko) | 2015-07-28 | 2018-03-16 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 감염을 예방하거나 치료하기 위한 베투인 유도체 |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017025901A1 (en) * | 2015-08-11 | 2017-02-16 | Hetero Research Foundation | Novel c28-analogues with c3-modifications of triterpene derivatives as hiv inhibitors |
| EA201890767A1 (ru) | 2015-09-23 | 2019-09-30 | Рита Фармасьютикалз, Инк. | C4-модифицированные производные олеаноловой кислоты для ингибирования il-17 и других применений |
| CN108368071A (zh) | 2015-09-24 | 2018-08-03 | 葛兰素史克知识产权第二有限公司 | 具有hiv成熟抑制活性的化合物 |
| TW201726133A (zh) | 2015-11-20 | 2017-08-01 | Ｖｉｉｖ醫療保健英國（Ｎｏ‧４）有限公司 | Ｈｉｖ成熟抑制劑調配物 |
| WO2017125870A1 (en) | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| 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 |
| EP3478703A1 (en) * | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| WO2018044822A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| MX2020001412A (es) | 2017-08-04 | 2020-08-03 | Ardelyx Inc | Compuestos y métodos para tratar la hiperpotasemia. |
| JP6926939B2 (ja) * | 2017-10-23 | 2021-08-25 | 東京エレクトロン株式会社 | 半導体装置の製造方法 |
| JP6977474B2 (ja) * | 2017-10-23 | 2021-12-08 | 東京エレクトロン株式会社 | 半導体装置の製造方法 |
| US20210347813A1 (en) | 2018-04-24 | 2021-11-11 | Viiv Healthcare Uk (No. 5) Limited | Compounds with hiv maturation inhibitory activity |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| EP3810141A1 (en) | 2018-06-20 | 2021-04-28 | Reata Pharmaceuticals, Inc. | Cysteine-dependent inverse agonists of nuclear receptors ror-gamma/ror-gamma-t and methods of treating diseases or disorders therewith |
| ES3039169T3 (en) | 2019-02-07 | 2025-10-17 | Ardelyx Inc | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| PL3924361T3 (pl) | 2019-02-11 | 2024-03-18 | Hetero Labs Limited | Nowe pochodne triterpenu jako inhibitory wirusa hiv |
| KR102891865B1 (ko) | 2019-07-19 | 2025-11-26 | 리아타 파마슈티컬즈, 아이엔씨. | C17 극성-치환된 헤테로방향족 합성 트리터페노이드 및 그의 사용 방법 |
| GB2598300A (en) * | 2020-08-21 | 2022-03-02 | Univ Durham | Cross-linking method and applications in bioconjugation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110015196A1 (en) * | 2009-07-14 | 2011-01-20 | Hetero Research Foundation | Lupeol-type triterpene derivatives as antivirals |
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| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| 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 |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| MXPA06010592A (es) | 2004-03-17 | 2007-06-12 | Panacos Pharmaceuticals Inc | Sales farmaceuticas de acido 3-o-(3',3'-dimetilsuccinil) betulinico. |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| US8067620B2 (en) | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
| WO2008127364A2 (en) * | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| US20110144069A1 (en) | 2006-10-16 | 2011-06-16 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| AU2009214779A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17beta lupane derivatives |
| BR112012030818A2 (pt) * | 2010-06-04 | 2019-09-24 | Bristol-Myers Squibb Company | "derivados de ácido c-3 betulínico modificado como inibidores da maturação do hiv" |
| WO2011153319A1 (en) * | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
-
2012
- 2012-01-27 JP JP2013551362A patent/JP6001560B2/ja active Active
- 2012-01-27 CN CN201280014966.XA patent/CN103429607B/zh active Active
- 2012-01-27 EA EA201391127A patent/EA022470B1/ru not_active IP Right Cessation
- 2012-01-27 PT PT127029478T patent/PT2670765T/pt unknown
- 2012-01-27 KR KR1020137023070A patent/KR101886467B1/ko not_active Expired - Fee Related
- 2012-01-27 PH PH1/2013/501528A patent/PH12013501528A1/en unknown
- 2012-01-27 PE PE2013001719A patent/PE20141152A1/es active IP Right Grant
- 2012-01-27 WO PCT/US2012/022852 patent/WO2012106190A1/en not_active Ceased
- 2012-01-27 SG SG2013056858A patent/SG192144A1/en unknown
- 2012-01-27 ES ES12702947.8T patent/ES2653847T3/es active Active
- 2012-01-27 EP EP12702947.8A patent/EP2670765B1/en active Active
- 2012-01-27 AU AU2012212509A patent/AU2012212509B2/en active Active
- 2012-01-27 BR BR112013019419A patent/BR112013019419A2/pt not_active Application Discontinuation
- 2012-01-27 CA CA2826113A patent/CA2826113C/en active Active
- 2012-01-27 MA MA36183A patent/MA34909B1/fr unknown
- 2012-01-27 US US13/359,727 patent/US8846647B2/en active Active
- 2012-01-27 MY MYPI2013701325A patent/MY162186A/en unknown
- 2012-01-31 TW TW101103140A patent/TWI628188B/zh not_active IP Right Cessation
- 2012-01-31 AR ARP120100314A patent/AR085053A1/es unknown
- 2012-01-31 UY UY0001033886A patent/UY33886A/es not_active Application Discontinuation
-
2013
- 2013-07-26 TN TNP2013000321A patent/TN2013000321A1/fr unknown
- 2013-07-28 IL IL227678A patent/IL227678B/en active IP Right Grant
- 2013-07-30 CL CL2013002185A patent/CL2013002185A1/es unknown
- 2013-08-27 CO CO13203030A patent/CO6751275A2/es unknown
- 2013-08-30 ZA ZA2013/06546A patent/ZA201306546B/en unknown
-
2014
- 2014-07-24 US US14/339,572 patent/US20140343000A1/en not_active Abandoned
-
2016
- 2016-02-04 US US15/015,741 patent/US20160151387A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110015196A1 (en) * | 2009-07-14 | 2011-01-20 | Hetero Research Foundation | Lupeol-type triterpene derivatives as antivirals |
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