WO2016077561A1 - Oxolupene derivatives - Google Patents
Oxolupene derivatives Download PDFInfo
- Publication number
- WO2016077561A1 WO2016077561A1 PCT/US2015/060344 US2015060344W WO2016077561A1 WO 2016077561 A1 WO2016077561 A1 WO 2016077561A1 US 2015060344 W US2015060344 W US 2015060344W WO 2016077561 A1 WO2016077561 A1 WO 2016077561A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- group
- mmol
- substituted
- cycloalkyl
- 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.)
- Ceased
Links
- 0 C*CC(NC)O Chemical compound C*CC(NC)O 0.000 description 6
- ZVHSHFALPFACCI-AYHUBICZSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(O)=O)=CC2)[C@]13C(CNCCN(C)C)O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(O)=O)=CC2)[C@]13C(CNCCN(C)C)O ZVHSHFALPFACCI-AYHUBICZSA-N 0.000 description 1
- XUGLMFTUDJJAHD-OYVOJWMQSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(NCCN(CC1)CCS1(=O)=O)=O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(NCCN(CC1)CCS1(=O)=O)=O XUGLMFTUDJJAHD-OYVOJWMQSA-N 0.000 description 1
- PJISZFWGQHNLJD-RHMOWCBVSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(O)=O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(O)=O PJISZFWGQHNLJD-RHMOWCBVSA-N 0.000 description 1
- WCIHWIGODJXGSR-TZTJMVJKSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13N Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13N WCIHWIGODJXGSR-TZTJMVJKSA-N 0.000 description 1
- IFYDVOCXXSCELL-CCUFPHSGSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O IFYDVOCXXSCELL-CCUFPHSGSA-N 0.000 description 1
- BLBXEDLFYYNFLP-UHBOBSHTSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CC[C@]4(CF)C(O)=O)=CC2)[C@]13C(O)=O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CC[C@]4(CF)C(O)=O)=CC2)[C@]13C(O)=O BLBXEDLFYYNFLP-UHBOBSHTSA-N 0.000 description 1
- JTYHFAVTVQGQCP-NFMGSKDISA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CC[C@]4(CF)C(O)=O)=CC2)[C@]13N Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CC[C@]4(CF)C(O)=O)=CC2)[C@]13N JTYHFAVTVQGQCP-NFMGSKDISA-N 0.000 description 1
- PFVJXZZYTPTQDT-VGCYNSABSA-N CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(O)=O)=CC2)[C@]13C(O)=O Chemical compound CC(C)C(C(C1)=O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c(cc4)ccc4C(O)=O)=CC2)[C@]13C(O)=O PFVJXZZYTPTQDT-VGCYNSABSA-N 0.000 description 1
- CZNQGOVXNBWUTQ-LLNBEGFRSA-N CC(C)C(C(C1)O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(NCCN1CCOCC1)=O Chemical compound CC(C)C(C(C1)O)=C([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)=CCC4C(O)=O)=CC2)[C@]13C(NCCN1CCOCC1)=O CZNQGOVXNBWUTQ-LLNBEGFRSA-N 0.000 description 1
- GBEQKGMRBPUAJW-JMIBCSSVSA-N CC(C)C(C(C[C@@]1(CC2)C(CNCCN(C)C)O)=O)=C1[C@@](C)(CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(OC)=O)=CC1 Chemical compound CC(C)C(C(C[C@@]1(CC2)C(CNCCN(C)C)O)=O)=C1[C@@](C)(CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(c(cc2)ccc2C(OC)=O)=CC1 GBEQKGMRBPUAJW-JMIBCSSVSA-N 0.000 description 1
- UZWQMHPVOYAYCC-UHFFFAOYSA-N CC(C1)N(C)CC1(F)F Chemical compound CC(C1)N(C)CC1(F)F UZWQMHPVOYAYCC-UHFFFAOYSA-N 0.000 description 1
- UMJWVRIJGCYYTH-UHFFFAOYSA-N CCOC(C(CF)=C)=O Chemical compound CCOC(C(CF)=C)=O UMJWVRIJGCYYTH-UHFFFAOYSA-N 0.000 description 1
- ULZCOWMSBOJCLT-UHFFFAOYSA-N CN(CC1)CCS1(=O)=O Chemical compound CN(CC1)CCS1(=O)=O ULZCOWMSBOJCLT-UHFFFAOYSA-N 0.000 description 1
- LOCIPSGHGSBQNW-UHFFFAOYSA-N CN(CC1)CS1(=O)=O Chemical compound CN(CC1)CS1(=O)=O LOCIPSGHGSBQNW-UHFFFAOYSA-N 0.000 description 1
- GKUNEXLMYIWURI-UHFFFAOYSA-N CN(CC1)N(CC=[IH])C1(F)F Chemical compound CN(CC1)N(CC=[IH])C1(F)F GKUNEXLMYIWURI-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N CN(CCC1)C1=O Chemical compound CN(CCC1)C1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N CN(CCCC1)C1=O Chemical compound CN(CCCC1)C1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- VWIIJDNADIEEDB-UHFFFAOYSA-N CN(CCO1)C1=O Chemical compound CN(CCO1)C1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 1
- KDTVWEHAAISPNW-UHFFFAOYSA-N CN1CCSCC1 Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 description 1
- ODYVYKAKFISAFQ-UHFFFAOYSA-N Cc1cc(N(C)C(OC2)=O)c2cc1 Chemical compound Cc1cc(N(C)C(OC2)=O)c2cc1 ODYVYKAKFISAFQ-UHFFFAOYSA-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
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- 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
Definitions
- R 4 or R5 can be selected from the group of -CORe, -COCOR 6 ,-S0 2 R7 and -SO2NR2R2;
- Any two adjacent R groups may combine to form an additional aryl, cycloalkyl, heteroaryl or heterocyclic ring fused to the ring initially bearing those R groups.
- substituted lower alkylamines e.g. hydroxyl-substituted alkylamines such as diethanolamine
- n 1-6;
- R22 and R23 are independently selected from the group of -H, -Ci-6 alkyl, -Ci-6 substituted alkyl, and -Ci-6 cycloalkyl,
- the mixture was stirred at -78 °C for a total of 2.5 h and was then lifted out of the cold bath and stirred for an additional 20 min at rt.
- the mixture was placed back in the -78 °C bath and to it was added with stirring 125 mL of saturated aqueous ammonium chloride.
- the resulting suspension was removed from the cold bath and allowed to come to rt while stirring.
- the mixture was concentrated in vacuum to remove the organic solvent, then to the mixture was added ethyl acetate (600 mL) and water (300 mL) and the mixture was shaken and the phases were separated.
- the organic layer was washed with water (2 x 200 mL) and with brine (50mL).
- Step 3 Preparation of ethyl 4-((3aR,5aR,5bR,7aR,l laS,l lbR,13aS)-3a-(2-((4- chlorobenzyl)(2-(dimethylamino)ethyl)amino)- 1 -hydroxyethyl)- 1 -isopropyl-
- a recombinant NL4-3 virus in which a section of the nef gene from NL4-3 was replaced with the Renilla luciferase gene, was used as a reference virus.
- residue Gag P373 was converted to P373S.
- the recombinant virus was prepared by transfection of the altered proviral clone of NL4-3. Transfections were performed in 293T cells using LipofectAMINE PLUS from Invitrogen (Carlsbad, CA), according to manufacturer's instruction. The virus was titered in MT-2 cells using luciferase enzyme activity as a marker.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/524,298 US9969767B2 (en) | 2014-11-14 | 2015-11-12 | Oxolupene derivatives |
| RU2017118489A RU2017118489A (ru) | 2014-11-14 | 2015-11-12 | Оксолупеновые производные |
| AU2015346303A AU2015346303B2 (en) | 2014-11-14 | 2015-11-12 | Oxolupene derivatives |
| BR112017009850A BR112017009850A2 (pt) | 2014-11-14 | 2015-11-12 | composto, composição, e, uso de uma quantidade melhoradora de hiv de um composto |
| JP2017525933A JP2017533937A (ja) | 2014-11-14 | 2015-11-12 | オキソルペン誘導体 |
| CN201580071098.2A CN107250153A (zh) | 2014-11-14 | 2015-11-12 | 氧代羽扇豆烯衍生物 |
| EP15798639.9A EP3218387A1 (en) | 2014-11-14 | 2015-11-12 | Oxolupene derivatives |
| KR1020177016222A KR20170087478A (ko) | 2014-11-14 | 2015-11-12 | 옥소루펜 유도체 |
| CA2967679A CA2967679A1 (en) | 2014-11-14 | 2015-11-12 | Oxolupene derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462079977P | 2014-11-14 | 2014-11-14 | |
| US62/079,977 | 2014-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2016077561A1 true WO2016077561A1 (en) | 2016-05-19 |
Family
ID=54697682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2015/060344 Ceased WO2016077561A1 (en) | 2014-11-14 | 2015-11-12 | Oxolupene derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9969767B2 (enExample) |
| EP (1) | EP3218387A1 (enExample) |
| JP (1) | JP2017533937A (enExample) |
| KR (1) | KR20170087478A (enExample) |
| CN (1) | CN107250153A (enExample) |
| AU (1) | AU2015346303B2 (enExample) |
| BR (1) | BR112017009850A2 (enExample) |
| CA (1) | CA2967679A1 (enExample) |
| RU (1) | RU2017118489A (enExample) |
| WO (1) | WO2016077561A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017017609A1 (en) * | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017607A1 (en) * | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017051355A1 (en) * | 2015-09-24 | 2017-03-30 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| WO2017125870A1 (en) * | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
Citations (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20050239748A1 (en) | 2004-03-17 | 2005-10-27 | Panacos Pharmaceuticals, Inc. | Pharmaceutical salts of 3-O-(3',3'-dimethylsuccinyl) betulinic acid |
| WO2006053255A2 (en) | 2004-11-12 | 2006-05-18 | Panacos Pharmaceuticals, Inc. | Novel betulin derivatives, preparation thereof and use thereof |
| US7354924B2 (en) | 2001-02-02 | 2008-04-08 | Bristol-Myers Squibb Company | 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 |
| US20080207573A1 (en) | 2006-10-16 | 2008-08-28 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| WO2009100532A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | NOVEL 17ß LUPANE DERIVATIVES |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| WO2011007230A2 (en) | 2009-07-14 | 2011-01-20 | Hetero Research Foundation | Lupeol-type triterpene derivatives as antivirals |
| US20110077227A1 (en) * | 2008-01-03 | 2011-03-31 | Christophe Moinet | Novel lupane derivatives |
| 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 |
| WO2011153315A1 (en) * | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| WO2012106188A1 (en) * | 2011-01-31 | 2012-08-09 | Bristol-Myers Squibb Company | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
| WO2013117137A1 (en) * | 2012-02-08 | 2013-08-15 | Jiangxi Qingfeng Pharmaceutical Inc. | Lupane triterpenoid derivatives and pharmaceutical use thereof |
| US20130210787A1 (en) | 2012-02-15 | 2013-08-15 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity |
| US8846647B2 (en) | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR063546A1 (es) * | 2006-11-03 | 2009-01-28 | Panacos Pharmaceuticals Inc | DERIVADOS DE TRITERPENO, METODOS PARA SU PREPARACION, COMPOSICIONES FARMACEUTICAS QUE LOS COMPRENDEN Y SU USO EN LA FABRICACION DE MEDICAMENTOS PARA EL TRATAMIENTO DE INFECCIoN POR EL VIRUS VIH. |
| WO2009082819A1 (en) * | 2008-01-03 | 2009-07-09 | Virochem Pharma Inc. | Novel lupane derivatives |
| EA201290632A1 (ru) * | 2010-02-11 | 2013-03-29 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Производные бетулина |
| JO3387B1 (ar) * | 2011-12-16 | 2019-03-13 | Glaxosmithkline Llc | مشتقات بيتولين |
-
2015
- 2015-11-12 US US15/524,298 patent/US9969767B2/en not_active Expired - Fee Related
- 2015-11-12 JP JP2017525933A patent/JP2017533937A/ja active Pending
- 2015-11-12 WO PCT/US2015/060344 patent/WO2016077561A1/en not_active Ceased
- 2015-11-12 KR KR1020177016222A patent/KR20170087478A/ko not_active Withdrawn
- 2015-11-12 RU RU2017118489A patent/RU2017118489A/ru not_active Application Discontinuation
- 2015-11-12 CA CA2967679A patent/CA2967679A1/en not_active Abandoned
- 2015-11-12 BR BR112017009850A patent/BR112017009850A2/pt not_active IP Right Cessation
- 2015-11-12 EP EP15798639.9A patent/EP3218387A1/en not_active Ceased
- 2015-11-12 AU AU2015346303A patent/AU2015346303B2/en not_active Ceased
- 2015-11-12 CN CN201580071098.2A patent/CN107250153A/zh active Pending
Patent Citations (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US7354924B2 (en) | 2001-02-02 | 2008-04-08 | Bristol-Myers Squibb Company | 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 |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| US20050239748A1 (en) | 2004-03-17 | 2005-10-27 | Panacos Pharmaceuticals, Inc. | Pharmaceutical salts of 3-O-(3',3'-dimethylsuccinyl) betulinic acid |
| WO2006053255A2 (en) | 2004-11-12 | 2006-05-18 | Panacos Pharmaceuticals, Inc. | Novel betulin derivatives, preparation thereof and use thereof |
| US20080207573A1 (en) | 2006-10-16 | 2008-08-28 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| US20110077227A1 (en) * | 2008-01-03 | 2011-03-31 | Christophe Moinet | Novel lupane derivatives |
| WO2009100532A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | NOVEL 17ß LUPANE DERIVATIVES |
| WO2011007230A2 (en) | 2009-07-14 | 2011-01-20 | Hetero Research Foundation | Lupeol-type triterpene derivatives as antivirals |
| 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 |
| WO2011153315A1 (en) * | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| US8754068B2 (en) | 2010-06-04 | 2014-06-17 | Bristol-Myers Squibb Company | Modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| US8802661B2 (en) | 2010-06-04 | 2014-08-12 | Bristol-Myers Squibb Company | C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| WO2012106188A1 (en) * | 2011-01-31 | 2012-08-09 | Bristol-Myers Squibb Company | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
| US8748415B2 (en) | 2011-01-31 | 2014-06-10 | Bristol-Myers Squibb Company | C-28 amines of C-3 modified betulinic acid derivatives as HIV maturation inhibitors |
| US8846647B2 (en) | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
| WO2013117137A1 (en) * | 2012-02-08 | 2013-08-15 | Jiangxi Qingfeng Pharmaceutical Inc. | Lupane triterpenoid derivatives and pharmaceutical use thereof |
| US20130210787A1 (en) | 2012-02-15 | 2013-08-15 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity |
| WO2013123019A1 (en) | 2012-02-15 | 2013-08-22 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity |
Non-Patent Citations (6)
| Title |
|---|
| CELL, vol. 9, 29 October 1999 (1999-10-29), pages 243 - 246 |
| DRUG DISCOVERY TODAY, vol. 5, no. 5, May 2000 (2000-05-01), pages 183 - 194 |
| DRUGS OF THE FUTURE, vol. 24, no. 12, 1999, pages 1355 - 1362 |
| KASHIWADA, Y. ET AL., J. MED. CHEM., vol. 39, 1996, pages 1016 - 1017 |
| NICHOLAS A.; KADOW, JOHN F.: "Inhibitors of the entry ofHIV into host cells. Meanwell", CURRENT OPINION IN DRUG DISCOVERY & DEVELOPMENT, vol. 6, no. 4, 2003, pages 451 - 461 |
| POKROVSKII, A. G. ET AL.: "Synthesis of derivatives of plant triterpenes and study of their antiviral and immunostimulating activity", KHIMIYA Y INTERESAKH USTOICHIVOGO RAZVITIYA, vol. 9, no. 3, 2001, pages 485 - 491, XP002534916 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017017609A1 (en) * | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017607A1 (en) * | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017051355A1 (en) * | 2015-09-24 | 2017-03-30 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| 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 |
| US20180273579A1 (en) * | 2015-09-24 | 2018-09-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| WO2017125870A1 (en) * | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015346303B2 (en) | 2018-03-15 |
| BR112017009850A2 (pt) | 2018-01-16 |
| US20170334946A1 (en) | 2017-11-23 |
| RU2017118489A3 (enExample) | 2019-02-13 |
| CA2967679A1 (en) | 2016-05-19 |
| CN107250153A (zh) | 2017-10-13 |
| JP2017533937A (ja) | 2017-11-16 |
| US9969767B2 (en) | 2018-05-15 |
| RU2017118489A (ru) | 2018-12-14 |
| KR20170087478A (ko) | 2017-07-28 |
| AU2015346303A1 (en) | 2017-06-08 |
| EP3218387A1 (en) | 2017-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2801491C (en) | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors | |
| AU2013221725B2 (en) | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity | |
| AU2014218754B2 (en) | C-3 alkyl and alkenyl modified betulinic acid derivatives useful in the treatment of HIV | |
| AU2013259894B2 (en) | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity | |
| WO2011153315A1 (en) | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors | |
| WO2015157483A1 (en) | Triterpenoids with hiv maturation inhibitory activity, substituted in position 3 by a non-aromatic ring carrying a haloalkyl substituent | |
| AU2015346303B2 (en) | Oxolupene derivatives | |
| WO2015195776A1 (en) | Betulinic acid derivatives with hiv maturation inhibitory activity | |
| AU2015346314B2 (en) | Extended betulinic acid analogs | |
| US10047118B2 (en) | C17-aryl substituted betulinic acid analogs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 15798639 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 15524298 Country of ref document: US |
|
| ENP | Entry into the national phase |
Ref document number: 2967679 Country of ref document: CA |
|
| ENP | Entry into the national phase |
Ref document number: 2017525933 Country of ref document: JP Kind code of ref document: A |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| REEP | Request for entry into the european phase |
Ref document number: 2015798639 Country of ref document: EP |
|
| REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112017009850 Country of ref document: BR |
|
| ENP | Entry into the national phase |
Ref document number: 2015346303 Country of ref document: AU Date of ref document: 20151112 Kind code of ref document: A |
|
| ENP | Entry into the national phase |
Ref document number: 20177016222 Country of ref document: KR Kind code of ref document: A |
|
| ENP | Entry into the national phase |
Ref document number: 2017118489 Country of ref document: RU Kind code of ref document: A |
|
| ENP | Entry into the national phase |
Ref document number: 112017009850 Country of ref document: BR Kind code of ref document: A2 Effective date: 20170510 |