CA2849475A1 - Novel betulinic acid derivatives with antiviral activity - Google Patents
Novel betulinic acid derivatives with antiviral activity Download PDFInfo
- Publication number
- CA2849475A1 CA2849475A1 CA2849475A CA2849475A CA2849475A1 CA 2849475 A1 CA2849475 A1 CA 2849475A1 CA 2849475 A CA2849475 A CA 2849475A CA 2849475 A CA2849475 A CA 2849475A CA 2849475 A1 CA2849475 A1 CA 2849475A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- aids
- hiv
- alkyl
- pharmaceutically acceptable
- 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.)
- Abandoned
Links
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 18
- 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 description 12
- 208000030507 AIDS Diseases 0.000 claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 8
- 239000003443 antiviral agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 229960005475 antiinfective agent Drugs 0.000 claims description 6
- 239000002955 immunomodulating agent Substances 0.000 claims description 6
- 229940121354 immunomodulator Drugs 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 230000002584 immunomodulator Effects 0.000 claims description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 35
- 230000035800 maturation Effects 0.000 abstract description 11
- 208000031886 HIV Infections Diseases 0.000 description 62
- 208000037357 HIV infectious disease Diseases 0.000 description 61
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 61
- -1 heteroalicyclic Chemical group 0.000 description 36
- 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 28
- 229960002555 zidovudine Drugs 0.000 description 23
- 125000001072 heteroaryl group Chemical group 0.000 description 19
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000003814 drug Substances 0.000 description 14
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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 11
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 10
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical class OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 102100034343 Integrase Human genes 0.000 description 9
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229960001936 indinavir Drugs 0.000 description 7
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 7
- 239000002777 nucleoside Substances 0.000 description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 108010019625 Atazanavir Sulfate Proteins 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 108010010369 HIV Protease Proteins 0.000 description 6
- 108010002350 Interleukin-2 Proteins 0.000 description 6
- 102000000588 Interleukin-2 Human genes 0.000 description 6
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 description 6
- 210000000234 capsid Anatomy 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
- 229960001355 tenofovir disoproxil Drugs 0.000 description 6
- 125000005296 thioaryloxy group Chemical group 0.000 description 6
- 125000005404 thioheteroaryloxy group Chemical group 0.000 description 6
- 125000005190 thiohydroxy group Chemical group 0.000 description 6
- 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 description 5
- 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 description 5
- FZAWPBDFRQGFGZ-UHFFFAOYSA-N 4-(2-chloroethyl)thiomorpholine Chemical compound ClCCN1CCSCC1 FZAWPBDFRQGFGZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 description 5
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 5
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- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 5
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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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161537099P | 2011-09-21 | 2011-09-21 | |
| US61/537,099 | 2011-09-21 | ||
| PCT/US2012/056186 WO2013043778A1 (en) | 2011-09-21 | 2012-09-20 | Novel betulinic acid derivatives with antiviral activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2849475A1 true CA2849475A1 (en) | 2013-03-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2849475A Abandoned CA2849475A1 (en) | 2011-09-21 | 2012-09-20 | Novel betulinic acid derivatives with antiviral activity |
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| Country | Link |
|---|---|
| US (1) | US8754069B2 (enExample) |
| EP (1) | EP2758419B8 (enExample) |
| JP (1) | JP6100786B2 (enExample) |
| KR (1) | KR20140069167A (enExample) |
| CN (1) | CN103814042B (enExample) |
| AU (1) | AU2012312485B2 (enExample) |
| BR (1) | BR112014006559A2 (enExample) |
| CA (1) | CA2849475A1 (enExample) |
| EA (1) | EA023463B1 (enExample) |
| ES (1) | ES2611727T3 (enExample) |
| IL (1) | IL231421A (enExample) |
| MX (1) | MX2014002936A (enExample) |
| SG (1) | SG11201400331WA (enExample) |
| TW (1) | TW201317255A (enExample) |
| WO (1) | WO2013043778A1 (enExample) |
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| 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 |
| JP2018512433A (ja) * | 2015-04-14 | 2018-05-17 | ヴィーブ ヘルスケア ユーケー（ナンバー４）リミテッド | Ｈｉｖ成熟阻害剤の製造方法 |
| RU2018105352A (ru) | 2015-07-28 | 2019-08-29 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Производные бетулина для предупреждения или лечения ВИЧ-инфекций |
| KR20180028534A (ko) | 2015-07-28 | 2018-03-16 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 감염을 예방하거나 치료하기 위한 베투인 유도체 |
| RU2018112958A (ru) | 2015-09-24 | 2019-10-28 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Соединения с ингибирующей созревание ВИЧ активностью |
| CN108699103A (zh) | 2016-01-20 | 2018-10-23 | 葛兰素史克知识产权第二有限公司 | 具有hiv成熟抑制活性的羽扇烷类的胺衍生物 |
| WO2018002847A1 (en) * | 2016-06-30 | 2018-01-04 | VIIV Healthcare UK (No.5) Limited | Aza-substituted inhibitors of human immunodeficiency virus replication |
| JP7436385B2 (ja) | 2018-04-24 | 2024-02-21 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | Ｈｉｖ成熟阻害活性を有する化合物 |
| WO2020006510A1 (en) * | 2018-06-29 | 2020-01-02 | Dfh Therapeutics | Triterpene amine derivatives |
| JP7648531B2 (ja) | 2019-02-11 | 2025-03-18 | ヘテロ ラボズ リミテッド | Ｈｉｖ阻害剤としての新規トリテルペン誘導体 |
| WO2021161206A1 (en) * | 2020-02-11 | 2021-08-19 | Hetero Labs Limited | Novel triterpene derivatives as hiv inhibitors |
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| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| 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 |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | 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 |
| 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 |
| 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 |
| WO2012106190A1 (en) | 2011-01-31 | 2012-08-09 | Bristol-Myers Squibb Company | C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity |
| JP2011511812A (ja) * | 2008-02-14 | 2011-04-14 | バイロケム ファーマ インコーポレイテッド | 新規１７βルパン誘導体 |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| BR112012030810A2 (pt) | 2010-06-04 | 2019-09-24 | Bristol-Myers Squibb Company | "c-28 amidas de derivados de ácido c-3 betulínico modificados como inibidores de maturação de hiv" |
| CA2801487C (en) | 2010-06-04 | 2017-12-05 | Bristol-Myers Squibb Company | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
| 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 |
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2012
- 2012-09-20 EP EP12766825.9A patent/EP2758419B8/en not_active Not-in-force
- 2012-09-20 WO PCT/US2012/056186 patent/WO2013043778A1/en not_active Ceased
- 2012-09-20 CA CA2849475A patent/CA2849475A1/en not_active Abandoned
- 2012-09-20 AU AU2012312485A patent/AU2012312485B2/en not_active Ceased
- 2012-09-20 KR KR1020147010087A patent/KR20140069167A/ko not_active Ceased
- 2012-09-20 EA EA201490643A patent/EA023463B1/ru not_active IP Right Cessation
- 2012-09-20 JP JP2014531936A patent/JP6100786B2/ja not_active Expired - Fee Related
- 2012-09-20 TW TW101134558A patent/TW201317255A/zh unknown
- 2012-09-20 US US13/623,165 patent/US8754069B2/en not_active Expired - Fee Related
- 2012-09-20 BR BR112014006559A patent/BR112014006559A2/pt not_active IP Right Cessation
- 2012-09-20 ES ES12766825.9T patent/ES2611727T3/es active Active
- 2012-09-20 MX MX2014002936A patent/MX2014002936A/es unknown
- 2012-09-20 CN CN201280046037.7A patent/CN103814042B/zh not_active Expired - Fee Related
- 2012-09-20 SG SG11201400331WA patent/SG11201400331WA/en unknown
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2014
- 2014-03-09 IL IL231421A patent/IL231421A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN103814042B (zh) | 2015-08-19 |
| US8754069B2 (en) | 2014-06-17 |
| IL231421A0 (en) | 2014-04-30 |
| CN103814042A (zh) | 2014-05-21 |
| BR112014006559A2 (pt) | 2017-03-28 |
| US20130072465A1 (en) | 2013-03-21 |
| MX2014002936A (es) | 2014-04-25 |
| JP6100786B2 (ja) | 2017-03-22 |
| EP2758419A1 (en) | 2014-07-30 |
| EA201490643A1 (ru) | 2014-06-30 |
| KR20140069167A (ko) | 2014-06-09 |
| AU2012312485A1 (en) | 2014-05-08 |
| EP2758419B8 (en) | 2017-04-19 |
| TW201317255A (zh) | 2013-05-01 |
| AU2012312485B2 (en) | 2016-09-01 |
| JP2014526554A (ja) | 2014-10-06 |
| SG11201400331WA (en) | 2014-08-28 |
| EA023463B1 (ru) | 2016-06-30 |
| IL231421A (en) | 2015-11-30 |
| WO2013043778A1 (en) | 2013-03-28 |
| ES2611727T3 (es) | 2017-05-10 |
| EP2758419B1 (en) | 2016-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20190920 |