ES2281960T3 - Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso. - Google Patents
Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso. Download PDFInfo
- Publication number
- ES2281960T3 ES2281960T3 ES99909758T ES99909758T ES2281960T3 ES 2281960 T3 ES2281960 T3 ES 2281960T3 ES 99909758 T ES99909758 T ES 99909758T ES 99909758 T ES99909758 T ES 99909758T ES 2281960 T3 ES2281960 T3 ES 2281960T3
- Authority
- ES
- Spain
- Prior art keywords
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- pharmaceutical composition
- betulin
- hydrogen
- substituted
- 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.)
- Expired - Lifetime
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- JZZMDHQYBFQRMW-ROUWMTJPSA-N (1s,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol Chemical compound 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 JZZMDHQYBFQRMW-ROUWMTJPSA-N 0.000 title description 23
- 238000002360 preparation method Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound 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 claims abstract description 51
- MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 claims abstract description 37
- JYDNKGUBLIKNAM-UHFFFAOYSA-N Oxyallobutulin Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C JYDNKGUBLIKNAM-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 229940079593 drug Drugs 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 230000001177 retroviral effect Effects 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 8
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003443 antiviral agent Substances 0.000 claims description 7
- 239000003022 immunostimulating agent Substances 0.000 claims description 7
- 108010002350 Interleukin-2 Proteins 0.000 claims description 6
- 102000000588 Interleukin-2 Human genes 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000000840 anti-viral effect Effects 0.000 claims description 6
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- 230000003308 immunostimulating effect Effects 0.000 claims description 6
- 239000002777 nucleoside Substances 0.000 claims description 6
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 6
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 6
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- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 4
- 229960005319 delavirdine Drugs 0.000 claims description 4
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- 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 claims description 4
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims description 4
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- 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 claims description 4
- 229960000884 nelfinavir Drugs 0.000 claims description 4
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 4
- 229960000689 nevirapine Drugs 0.000 claims description 4
- 229960000311 ritonavir Drugs 0.000 claims description 4
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 4
- 229960001852 saquinavir Drugs 0.000 claims description 4
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 102000008070 Interferon-gamma Human genes 0.000 claims description 3
- 108010074328 Interferon-gamma Proteins 0.000 claims description 3
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 3
- 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 claims description 3
- 229960004748 abacavir Drugs 0.000 claims description 3
- 229960001997 adefovir Drugs 0.000 claims description 3
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 3
- 229960001830 amprenavir Drugs 0.000 claims description 3
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
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- 108010074605 gamma-Globulins Proteins 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229960003130 interferon gamma Drugs 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 229960000329 ribavirin Drugs 0.000 claims description 3
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims 4
- GTBVPNLDJICROQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one;guanidine Chemical compound NC(N)=N.C1=CC=C2NC(O)=NC2=C1 GTBVPNLDJICROQ-UHFFFAOYSA-N 0.000 claims 2
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 2
- 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 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims 2
- DLGSOJOOYHWROO-WQLSENKSSA-N [(z)-(1-methyl-2-oxoindol-3-ylidene)amino]thiourea Chemical compound C1=CC=C2N(C)C(=O)\C(=N/NC(N)=S)C2=C1 DLGSOJOOYHWROO-WQLSENKSSA-N 0.000 claims 2
- 229960004150 aciclovir Drugs 0.000 claims 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
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- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 2
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- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 35
- 230000000694 effects Effects 0.000 description 32
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- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound 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 description 13
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- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 description 8
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- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 6
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000010415 tropism Effects 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 230000007502 viral entry Effects 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 235000020138 yakult Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7644998P | 1998-03-02 | 1998-03-02 | |
| US76449P | 1998-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2281960T3 true ES2281960T3 (es) | 2007-10-01 |
Family
ID=22132095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99909758T Expired - Lifetime ES2281960T3 (es) | 1998-03-02 | 1999-03-02 | Derivados acilados de betulina y dihidrobetulina, su preparacion y su uso. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6172110B1 (enExample) |
| EP (1) | EP1068219B1 (enExample) |
| JP (1) | JP2002505337A (enExample) |
| AT (1) | ATE348839T1 (enExample) |
| AU (1) | AU762404B2 (enExample) |
| CA (1) | CA2322868C (enExample) |
| DE (1) | DE69934486T2 (enExample) |
| DK (1) | DK1068219T3 (enExample) |
| ES (1) | ES2281960T3 (enExample) |
| NZ (1) | NZ506623A (enExample) |
| PT (1) | PT1068219E (enExample) |
| WO (1) | WO1999045025A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6232481B1 (en) * | 2000-01-11 | 2001-05-15 | Regents Of The University Of Minnesota | Method for manufacturing betulinic acid |
| US6656970B2 (en) * | 2000-05-11 | 2003-12-02 | Dabur Research Foundation | Method and compositions for solubilization of pentacyclic triterpenes |
| US7365221B2 (en) * | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US20040131629A1 (en) * | 2002-09-26 | 2004-07-08 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US7537765B2 (en) * | 2003-01-29 | 2009-05-26 | Panacos Pharmaceuticals, Inc. | Inhibition of HIV-1 replication by disruption of the processing of the viral capsid-spacer peptide 1 protein |
| JP2006520756A (ja) * | 2003-01-29 | 2006-09-14 | パナコス ファーマシューティカルズ インコーポレーティッド | ウイルスキャプシドスペーサーペプチド１タンパク質のプロセシングの破壊によるｈｉｖ−１複製の阻害 |
| US7026305B2 (en) * | 2003-04-14 | 2006-04-11 | Meharry Medical College | Anti-HIV agents with dual sites of action |
| MXPA06010592A (es) * | 2004-03-17 | 2007-06-12 | Panacos Pharmaceuticals Inc | Sales farmaceuticas de acido 3-o-(3',3'-dimetilsuccinil) betulinico. |
| US7776863B2 (en) * | 2004-03-24 | 2010-08-17 | Bristol-Myers Squibb Company | Methods of treating HIV infection |
| US20050215544A1 (en) * | 2004-03-24 | 2005-09-29 | Pin-Fang Lin | Methods of treating HIV infection |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| US7282521B2 (en) * | 2004-05-24 | 2007-10-16 | University Of North Carolina At Chapel Hill | Anti-retroviral moronic acid derivatives |
| CA2607177A1 (en) * | 2004-09-10 | 2006-03-23 | Brij B. Saxena | Betulinol derivatives as anti-cancer agents |
| TW200628161A (en) * | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| JP2008535923A (ja) * | 2005-04-12 | 2008-09-04 | パナコス ファーマシューティカルズ インコーポレーティッド | ３−ｏ−（３’，３’−ジメチルスクシニル）ベツリン酸ジ−ｎ−メチル−ｄ−グルカミンの多形 |
| FI121468B (fi) * | 2006-06-07 | 2010-11-30 | Valtion Teknillinen | Betuliiniperäiset yhdisteet antimikrobisina aineina |
| US20080039428A1 (en) * | 2006-06-29 | 2008-02-14 | Panacos Pharmaceuticals, Inc. | Antiretroviral combination therapy |
| 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. |
| US20110152229A1 (en) * | 2006-11-22 | 2011-06-23 | Duke University | Betulinic acid derivatives as anti-hiv agents |
| US8269026B2 (en) * | 2008-01-03 | 2012-09-18 | Vertex Pharmaceuticals Incorporated | Lupane derivatives useful for treating HIV |
| KR100941595B1 (ko) * | 2008-06-05 | 2010-02-11 | 주식회사 알앤엘바이오 | 바이러스 억제제로서 유용한 트리테르페노이드계 화합물 |
| US20100104669A1 (en) * | 2008-10-28 | 2010-04-29 | Scheffler Armin | Method for preparing an aqueous solution containing triterpenic acid, aqueous solution containing triterpenic acid, and use thereof |
| MX2012013628A (es) * | 2010-06-04 | 2012-12-17 | Bristol Myers Squibb Co | Amidas c-28 de derivados del acido betulinico c-3 modificados como inhibidores de la maduracion del virus de inmunodeficiencia humana (vih). |
| CN103038245B (zh) * | 2010-06-04 | 2015-03-25 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
| RU2496785C1 (ru) * | 2012-09-24 | 2013-10-27 | Федеральное государственное бюджетное учреждение науки Институт технической химии Уральского отделения Российской академии наук (ИТХ УрО РАН) | Тритерпеноиды с фрагментом ен-нитрила в а-пентацикле |
| PL227790B1 (pl) | 2015-08-13 | 2018-01-31 | Slaski Univ Medyczny W Katowicach | Fosfoniany acetylenowych pochodnych betuliny o działaniu przeciwnowotworowym, sposób ich wytwarzania i zastosowanie. |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01143832A (ja) * | 1987-12-01 | 1989-06-06 | Toa Nenryo Kogyo Kk | 制癌剤 |
| FR2683531B1 (fr) * | 1991-11-13 | 1993-12-31 | Rhone Poulenc Rorer Sa | Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| US5679828A (en) * | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
-
1999
- 1999-03-02 PT PT99909758T patent/PT1068219E/pt unknown
- 1999-03-02 AT AT99909758T patent/ATE348839T1/de not_active IP Right Cessation
- 1999-03-02 DK DK99909758T patent/DK1068219T3/da active
- 1999-03-02 JP JP2000534567A patent/JP2002505337A/ja active Pending
- 1999-03-02 WO PCT/US1999/004605 patent/WO1999045025A1/en not_active Ceased
- 1999-03-02 AU AU28894/99A patent/AU762404B2/en not_active Ceased
- 1999-03-02 CA CA002322868A patent/CA2322868C/en not_active Expired - Fee Related
- 1999-03-02 US US09/260,078 patent/US6172110B1/en not_active Expired - Fee Related
- 1999-03-02 EP EP99909758A patent/EP1068219B1/en not_active Expired - Lifetime
- 1999-03-02 ES ES99909758T patent/ES2281960T3/es not_active Expired - Lifetime
- 1999-03-02 DE DE69934486T patent/DE69934486T2/de not_active Expired - Fee Related
- 1999-03-02 NZ NZ506623A patent/NZ506623A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2322868A1 (en) | 1999-09-10 |
| AU2889499A (en) | 1999-09-20 |
| CA2322868C (en) | 2009-02-03 |
| NZ506623A (en) | 2002-10-25 |
| JP2002505337A (ja) | 2002-02-19 |
| EP1068219A4 (en) | 2005-05-25 |
| DE69934486D1 (de) | 2007-02-01 |
| DK1068219T3 (da) | 2007-04-30 |
| EP1068219B1 (en) | 2006-12-20 |
| AU762404B2 (en) | 2003-06-26 |
| DE69934486T2 (de) | 2007-10-04 |
| US6172110B1 (en) | 2001-01-09 |
| PT1068219E (pt) | 2007-03-30 |
| EP1068219A1 (en) | 2001-01-17 |
| ATE348839T1 (de) | 2007-01-15 |
| WO1999045025A1 (en) | 1999-09-10 |
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