EA023578B1 - C28-амины c3-модифицированных производных бетулиновой кислоты в качестве ингибиторов созревания вич - Google Patents
C28-амины c3-модифицированных производных бетулиновой кислоты в качестве ингибиторов созревания вич Download PDFInfo
- Publication number
- EA023578B1 EA023578B1 EA201391098A EA201391098A EA023578B1 EA 023578 B1 EA023578 B1 EA 023578B1 EA 201391098 A EA201391098 A EA 201391098A EA 201391098 A EA201391098 A EA 201391098A EA 023578 B1 EA023578 B1 EA 023578B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- group
- methyl
- prop
- pentamethyl
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title abstract description 246
- 239000003112 inhibitor Substances 0.000 title abstract description 37
- 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 description 11
- 230000035800 maturation Effects 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 409
- 150000001875 compounds Chemical class 0.000 claims abstract description 290
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 282
- 125000000217 alkyl group Chemical group 0.000 claims description 140
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000004429 atom Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 229940110676 inzo Drugs 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 abstract description 84
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- -1 -C 3-6 cycloalkyl Chemical group 0.000 description 675
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 339
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- 235000010233 benzoic acid Nutrition 0.000 description 234
- 239000005711 Benzoic acid Substances 0.000 description 218
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 214
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
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- 239000000047 product Substances 0.000 description 131
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 105
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 97
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 91
- 239000002904 solvent Substances 0.000 description 88
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 81
- 230000007062 hydrolysis Effects 0.000 description 79
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- 208000037357 HIV infectious disease Diseases 0.000 description 65
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 65
- 230000002829 reductive effect Effects 0.000 description 54
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- 239000012043 crude product Substances 0.000 description 52
- 238000002953 preparative HPLC Methods 0.000 description 50
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 44
- 238000000746 purification Methods 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 40
- 239000012044 organic layer Substances 0.000 description 37
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- 239000000126 substance Substances 0.000 description 34
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- 239000000706 filtrate Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
- 238000001914 filtration Methods 0.000 description 24
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000002274 desiccant Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 17
- 150000001559 benzoic acids Chemical class 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000006260 foam Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
- PDLNHDSYGLTYDS-UHFFFAOYSA-N 3-aminopropanoic acid;hydrochloride Chemical compound Cl.NCCC(O)=O PDLNHDSYGLTYDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000005903 acid hydrolysis reaction Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
- 125000003373 pyrazinyl group Chemical group 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 241000700605 Viruses Species 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 229910002027 silica gel Inorganic materials 0.000 description 12
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- 239000003795 chemical substances by application Substances 0.000 description 11
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
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- 235000019257 ammonium acetate Nutrition 0.000 description 10
- 229940043376 ammonium acetate Drugs 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 9
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- 229940002612 prodrug Drugs 0.000 description 9
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- 108090000565 Capsid Proteins Proteins 0.000 description 8
- 102100023321 Ceruloplasmin Human genes 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
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- 238000006268 reductive amination reaction Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 208000007766 Kaposi sarcoma Diseases 0.000 description 7
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical class 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 description 7
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- VRXIOAYUQIITBU-UHFFFAOYSA-N tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CCO)CC1 VRXIOAYUQIITBU-UHFFFAOYSA-N 0.000 description 1
- PNQYAMWGTGWJDW-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)-n-methylcarbamate Chemical compound NCCCN(C)C(=O)OC(C)(C)C PNQYAMWGTGWJDW-UHFFFAOYSA-N 0.000 description 1
- XJJBXZIKXFOMLP-UHFFFAOYSA-N tert-butyl pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCN1 XJJBXZIKXFOMLP-UHFFFAOYSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
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- PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437870P | 2011-01-31 | 2011-01-31 | |
| PCT/US2012/022847 WO2012106188A1 (en) | 2011-01-31 | 2012-01-27 | C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201391098A1 EA201391098A1 (ru) | 2013-12-30 |
| EA023578B1 true EA023578B1 (ru) | 2016-06-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| EA201391098A EA023578B1 (ru) | 2011-01-31 | 2012-01-27 | C28-амины c3-модифицированных производных бетулиновой кислоты в качестве ингибиторов созревания вич |
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|---|---|
| US (1) | US8748415B2 (enExample) |
| EP (1) | EP2670764B1 (enExample) |
| JP (1) | JP6000283B2 (enExample) |
| CN (1) | CN103339141B (enExample) |
| BR (1) | BR112014010105A2 (enExample) |
| CA (1) | CA2826257A1 (enExample) |
| CY (1) | CY1116989T1 (enExample) |
| DK (1) | DK2670764T3 (enExample) |
| EA (1) | EA023578B1 (enExample) |
| ES (1) | ES2552512T3 (enExample) |
| HR (1) | HRP20151212T1 (enExample) |
| HU (1) | HUE026371T2 (enExample) |
| MX (1) | MX2013008359A (enExample) |
| PL (1) | PL2670764T3 (enExample) |
| PT (1) | PT2670764E (enExample) |
| RS (1) | RS54352B1 (enExample) |
| SI (1) | SI2670764T1 (enExample) |
| SM (1) | SMT201500303B (enExample) |
| WO (1) | WO2012106188A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2014002936A (es) | 2011-09-21 | 2014-04-25 | Bristol Myers Squibb Co | Nuevos derivados de acido betulinico con actividad antiviral. |
| 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 |
| RU2519133C1 (ru) * | 2012-11-09 | 2014-06-10 | Леонид Леонидович Клопотенко | Мазь, содержащая инкапсулированную тритерпеновую кислоту или ее производные |
| RU2516952C1 (ru) * | 2012-11-09 | 2014-05-20 | Леонид Леонидович Клопотенко | Фармацевтическая композиция, содержащая инкапсулированную тритерпеновую кислоту или ее производные |
| CN103214543B (zh) * | 2012-12-25 | 2015-09-02 | 中国人民解放军海军医学研究所 | 新山楂酸衍生物、其制备方法及其在抗肿瘤药物中的应用 |
| JP6186010B2 (ja) | 2013-02-06 | 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 | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| KR20150121712A (ko) * | 2013-02-25 | 2015-10-29 | 브리스톨-마이어스 스큅 컴퍼니 | Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체 |
| UY36070A (es) | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| WO2015195776A1 (en) * | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| CN107250152A (zh) | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | C17‑芳基取代的桦木酸类似物 |
| US9969767B2 (en) | 2014-11-14 | 2018-05-15 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| AU2015346314B2 (en) * | 2014-11-14 | 2018-04-12 | VIIV Healthcare UK (No.5) Limited | Extended betulinic acid analogs |
| EP3283467A1 (en) * | 2015-04-14 | 2018-02-21 | VIIV Healthcare UK(No.4) Limited | Methods of producing an hiv maturation inhibitor |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| KR20180054826A (ko) | 2015-09-24 | 2018-05-24 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 성숙 억제 활성을 갖는 화합물 |
| EP3405474A1 (en) | 2016-01-20 | 2018-11-28 | 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 |
| IL273078B2 (en) | 2017-09-13 | 2025-06-01 | Emmyon Inc | Ursolic acid morpholine and diethanolamine salts |
| MX2020002884A (es) | 2017-09-14 | 2020-10-05 | Phoenix Biotechnology Inc | Método y composición neuroprotectora mejorada para tratar afecciones neurológicas. |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
| US10343997B1 (en) | 2018-12-04 | 2019-07-09 | King Saud University | Ursolic acid derivatives |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| KR20220151038A (ko) | 2020-03-31 | 2022-11-11 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 예방를 위한 조성물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006053255A2 (en) * | 2004-11-12 | 2006-05-18 | Panacos Pharmaceuticals, Inc. | Novel betulin derivatives, preparation thereof and use thereof |
| WO2011153315A1 (en) * | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| 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 |
Family Cites Families (15)
| 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 |
| 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 |
| 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 |
| BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
| CN101142227A (zh) * | 2004-11-12 | 2008-03-12 | 帕纳克斯医药公司 | 新颖的桦木醇衍生物、其制备和其用途 |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| CA2714049A1 (en) * | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| US8846647B2 (en) * | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
-
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- 2012-01-27 ES ES12702946.0T patent/ES2552512T3/es active Active
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- 2012-01-27 EP EP12702946.0A patent/EP2670764B1/en active Active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006053255A2 (en) * | 2004-11-12 | 2006-05-18 | Panacos Pharmaceuticals, Inc. | Novel betulin derivatives, preparation thereof and use thereof |
| WO2011153315A1 (en) * | 2010-06-04 | 2011-12-08 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| ZHU Y.-M. ET AL.: "Synthesis and Anti-HIV Activity of Oleanolic Acid Derivatives", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 11, no. 24, 1 December 2001 (2001-12-01), pages 3115-3118, XP002984538, ISSN: 0960-894X, DOI: 10.1016/S0960-894X(01)00647-3, page 3116; table 1; compounds 18-20 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL2670764T3 (pl) | 2016-02-29 |
| SMT201500303B (it) | 2016-01-08 |
| CN103339141A (zh) | 2013-10-02 |
| PT2670764E (pt) | 2015-11-20 |
| HRP20151212T1 (hr) | 2015-12-04 |
| JP2014507422A (ja) | 2014-03-27 |
| ES2552512T3 (es) | 2015-11-30 |
| US8748415B2 (en) | 2014-06-10 |
| BR112014010105A2 (pt) | 2017-06-13 |
| CA2826257A1 (en) | 2012-08-09 |
| WO2012106188A1 (en) | 2012-08-09 |
| HUE026371T2 (en) | 2016-05-30 |
| JP6000283B2 (ja) | 2016-09-28 |
| DK2670764T3 (en) | 2015-12-07 |
| EP2670764B1 (en) | 2015-09-02 |
| RS54352B1 (sr) | 2016-02-29 |
| MX2013008359A (es) | 2013-08-27 |
| US20130029954A1 (en) | 2013-01-31 |
| CN103339141B (zh) | 2016-08-24 |
| CY1116989T1 (el) | 2017-04-05 |
| EA201391098A1 (ru) | 2013-12-30 |
| SI2670764T1 (sl) | 2016-03-31 |
| EP2670764A1 (en) | 2013-12-11 |
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