AU2017215529B2 - C-3 and C-17 modified triterpenoids as HIV-1 inhibitors - Google Patents
C-3 and C-17 modified triterpenoids as HIV-1 inhibitors Download PDFInfo
- Publication number
- AU2017215529B2 AU2017215529B2 AU2017215529A AU2017215529A AU2017215529B2 AU 2017215529 B2 AU2017215529 B2 AU 2017215529B2 AU 2017215529 A AU2017215529 A AU 2017215529A AU 2017215529 A AU2017215529 A AU 2017215529A AU 2017215529 B2 AU2017215529 B2 AU 2017215529B2
- Authority
- AU
- Australia
- Prior art keywords
- ethyl
- alkyl
- methyl
- group
- cyclohex
- 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.)
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- 0 CCOC(C(COc1ccncc1)(CC1)CC=C1C(C(C)(C)[C@]1CC2)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@](C)(CC2)[C@]1[C@@]([C@@](CC1)*(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)=O Chemical compound CCOC(C(COc1ccncc1)(CC1)CC=C1C(C(C)(C)[C@]1CC2)=CC[C@]1(C)[C@@](CC1)[C@]2(C)[C@](C)(CC2)[C@]1[C@@]([C@@](CC1)*(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)=O 0.000 description 7
- IWTFOFMTUOBLHG-UHFFFAOYSA-N COc1ncccc1 Chemical compound COc1ncccc1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 2
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- LXHQSMQHDLYODG-GQYLZUTBSA-N CC(C)(C)[SiH-](C)(C)OC(C(COc1cc(C#N)ccn1)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=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@@]21NCCN(CC1)CCS1(=O)=O)=O Chemical compound CC(C)(C)[SiH-](C)(C)OC(C(COc1cc(C#N)ccn1)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=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@@]21NCCN(CC1)CCS1(=O)=O)=O LXHQSMQHDLYODG-GQYLZUTBSA-N 0.000 description 1
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- YAXLTIIYMIBCBD-LYRXIKAQSA-N CC(C)([C@@H]1CC2)C(C(CC3)=CC[C@@]3(COc3cc(C(N)=O)ccn3)C(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@@]21NCCN(CC1)CCS1(=C)=O Chemical compound CC(C)([C@@H]1CC2)C(C(CC3)=CC[C@@]3(COc3cc(C(N)=O)ccn3)C(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@@]21NCCN(CC1)CCS1(=C)=O YAXLTIIYMIBCBD-LYRXIKAQSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- ANEPQSRPMPZCJG-XNYYGWFZSA-N CCC(C)(C)[C@H](CC1)C[C@@H](CC2)[C@]1(C)[C@](C)(CC1)[C@H]2[C@@H]([C@@H](CC2)C(C)=C)[C@@]12NCC[C@](CC1)(CC[C@H]1/S(/C)=C\C)O Chemical compound CCC(C)(C)[C@H](CC1)C[C@@H](CC2)[C@]1(C)[C@](C)(CC1)[C@H]2[C@@H]([C@@H](CC2)C(C)=C)[C@@]12NCC[C@](CC1)(CC[C@H]1/S(/C)=C\C)O ANEPQSRPMPZCJG-XNYYGWFZSA-N 0.000 description 1
- QDMVZZDMTRLIRU-WKJMJWHUSA-N CCCC(CC1)(CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H](CCC1)[C@@]21NCCN(CC1)CCS1(=O)=O)C(O[IH]C)=O Chemical compound CCCC(CC1)(CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H](CCC1)[C@@]21NCCN(CC1)CCS1(=O)=O)C(O[IH]C)=O QDMVZZDMTRLIRU-WKJMJWHUSA-N 0.000 description 1
- FRMCJMNDSLPABX-HGNWAPGBSA-N CCCN[C@@](CCC1)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(C(CC2)=CCC2(CCO)C(O[IH+])=O)=CC1 Chemical compound CCCN[C@@](CCC1)(CC2)[C@H]1[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@]1(C)[C@@H]2C(C)(C)C(C(CC2)=CCC2(CCO)C(O[IH+])=O)=CC1 FRMCJMNDSLPABX-HGNWAPGBSA-N 0.000 description 1
- SAWGAGUFXALJSN-UHFFFAOYSA-N CCOC(C(COc1cccnc1)(CC1)CCC1=O)=O Chemical compound CCOC(C(COc1cccnc1)(CC1)CCC1=O)=O SAWGAGUFXALJSN-UHFFFAOYSA-N 0.000 description 1
- KFAFWXMBYHSPPE-UHFFFAOYSA-N CCOC(C(COc1n[s]c(C)n1)(CC1)CC=C1OS(C(C)(F)F)(=O)=O)=O Chemical compound CCOC(C(COc1n[s]c(C)n1)(CC1)CC=C1OS(C(C)(F)F)(=O)=O)=O KFAFWXMBYHSPPE-UHFFFAOYSA-N 0.000 description 1
- WSECIHBJJSNTLN-MQPCXPQTSA-N CCOC(C(COc1n[s]c2ccccc12)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)C1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)=O Chemical compound CCOC(C(COc1n[s]c2ccccc12)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)C1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)=O WSECIHBJJSNTLN-MQPCXPQTSA-N 0.000 description 1
- SIBQYEWXIHNMSW-GLKNVHPNSA-N CCOC(C(COc1ncccc1)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21N)=O Chemical compound CCOC(C(COc1ncccc1)(CC1)CC=C1C(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C=C)[C@@]21N)=O SIBQYEWXIHNMSW-GLKNVHPNSA-N 0.000 description 1
- YPBJSWQUZUOQTP-UHFFFAOYSA-N CCOC(C(COc1nnccc1)(CC1)CC=C1OS(C(C)(F)F)(=O)=O)=O Chemical compound CCOC(C(COc1nnccc1)(CC1)CC=C1OS(C(C)(F)F)(=O)=O)=O YPBJSWQUZUOQTP-UHFFFAOYSA-N 0.000 description 1
- LYIVMMJJDDAKHV-UHFFFAOYSA-N CCOC(C(COc1nnccc1)(CC1)CCC11OCCO1)=O Chemical compound CCOC(C(COc1nnccc1)(CC1)CCC11OCCO1)=O LYIVMMJJDDAKHV-UHFFFAOYSA-N 0.000 description 1
- APPDKTZPGQTNMZ-UHFFFAOYSA-N CCOC(C1(CO[AlH2])CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O Chemical compound CCOC(C1(CO[AlH2])CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O APPDKTZPGQTNMZ-UHFFFAOYSA-N 0.000 description 1
- HPMJRIJHVUWHFQ-UHFFFAOYSA-N CCOC(C1(COc2n[nH]c(C(F)(F)F)c2)CC=C(C)CC1)=O Chemical compound CCOC(C1(COc2n[nH]c(C(F)(F)F)c2)CC=C(C)CC1)=O HPMJRIJHVUWHFQ-UHFFFAOYSA-N 0.000 description 1
- PMJHDCLMHDVZBC-UHFFFAOYSA-N CCOC(C1(COc2ncc[s]2)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O Chemical compound CCOC(C1(COc2ncc[s]2)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O PMJHDCLMHDVZBC-UHFFFAOYSA-N 0.000 description 1
- CTFYVTMOCCQPIW-UHFFFAOYSA-N CCOC(C1(COc2nnn[n]2C)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O Chemical compound CCOC(C1(COc2nnn[n]2C)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O CTFYVTMOCCQPIW-UHFFFAOYSA-N 0.000 description 1
- HKWNDPJOJRYGBK-QHCPKHFHSA-N CCOC([C@@]1(COC(c2ccccc2)=O)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O Chemical compound CCOC([C@@]1(COC(c2ccccc2)=O)CC=C(B2OC(C)(C)C(C)(C)O2)CC1)=O HKWNDPJOJRYGBK-QHCPKHFHSA-N 0.000 description 1
- REXLXWHMULJQCF-AZEOCICYSA-N CC[C@@](C)([C@@H](CC1)C(C)(C)C)[C@@H](CC2)[C@]1(C)[C@](C)(CC1)[C@H]2[C@@H]([C@@H](CC2)C(C)=C)[C@@]12NCCC(CC1)(CCS1(=O)=O)O Chemical compound CC[C@@](C)([C@@H](CC1)C(C)(C)C)[C@@H](CC2)[C@]1(C)[C@](C)(CC1)[C@H]2[C@@H]([C@@H](CC2)C(C)=C)[C@@]12NCCC(CC1)(CCS1(=O)=O)O REXLXWHMULJQCF-AZEOCICYSA-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
- PNEVJLFDIQAJEQ-KYZUINATSA-N CS([C@H](CC1)CC[C@]1(CC=O)O)(=O)=O Chemical compound CS([C@H](CC1)CC[C@]1(CC=O)O)(=O)=O PNEVJLFDIQAJEQ-KYZUINATSA-N 0.000 description 1
- XWLAESWNAXJIBN-UHFFFAOYSA-N O=C(CCOC(c1ccccc1)=O)OCc1ccccc1 Chemical compound O=C(CCOC(c1ccccc1)=O)OCc1ccccc1 XWLAESWNAXJIBN-UHFFFAOYSA-N 0.000 description 1
- KVRNTZJMJGLFML-UHFFFAOYSA-N [Tl]N(c1ccccc1)[Tl] Chemical compound [Tl]N(c1ccccc1)[Tl] KVRNTZJMJGLFML-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
-
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
- C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
- C12N9/503—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from viruses
- C12N9/506—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from viruses derived from RNA viruses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16211—Human Immunodeficiency Virus, HIV concerning HIV gagpol
- C12N2740/16222—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662291298P | 2016-02-04 | 2016-02-04 | |
| US62/291,298 | 2016-02-04 | ||
| PCT/IB2017/050568 WO2017134596A1 (en) | 2016-02-04 | 2017-02-02 | C-3 and c-17 modified triterpenoids as hiv-1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2017215529A1 AU2017215529A1 (en) | 2018-08-23 |
| AU2017215529A8 AU2017215529A8 (en) | 2018-08-30 |
| AU2017215529B2 true AU2017215529B2 (en) | 2019-01-31 |
Family
ID=57995251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2017215529A Active AU2017215529B2 (en) | 2016-02-04 | 2017-02-02 | C-3 and C-17 modified triterpenoids as HIV-1 inhibitors |
Country Status (39)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| UY38982A (es) | 2019-12-09 | 2021-06-30 | Viiv Healthcare Co | Composiciones farmacéuticas |
| WO2025068743A1 (en) | 2023-09-27 | 2025-04-03 | ViiV Healthcare UK (No.3) Limited | Pharmaceutical composition of cabotegravir |
| WO2024089216A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Novel sulfur-containing heteroaryl carboxamide compounds |
| WO2025037232A1 (en) | 2023-08-11 | 2025-02-20 | ViiV Healthcare UK (No.4) Limited | Tosylate salt form of a maturation inhibitor for treatment of hiv |
| CN121909019A (zh) | 2023-09-27 | 2026-04-21 | Viiv保健英国第三有限公司 | 药物组合物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014123889A1 (en) * | 2013-02-06 | 2014-08-14 | Bristol-Myers Squibb Company | C-19 modified triterpenoids with hiv maturation inhibitory activity |
| WO2015157483A1 (en) * | 2014-04-11 | 2015-10-15 | Bristol-Myers Squibb Company | Triterpenoids with hiv maturation inhibitory activity, substituted in position 3 by a non-aromatic ring carrying a haloalkyl substituent |
Family Cites Families (27)
| 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 |
| 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 |
| GB0301227D0 (en) | 2003-01-20 | 2003-02-19 | Keen Group Ltd | Seating apparatus |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| EP1730163A4 (en) | 2004-03-17 | 2009-12-30 | Panacos Pharmaceuticals Inc | Pharmaceutical salts of 3-O- (3,3-dimethylsuccinyl) betulinic acid |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
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