CA2711420A1 - Novel c-21-keto lupane derivatives preparation and use thereof - Google Patents
Novel c-21-keto lupane derivatives preparation and use thereof Download PDFInfo
- Publication number
- CA2711420A1 CA2711420A1 CA2711420A CA2711420A CA2711420A1 CA 2711420 A1 CA2711420 A1 CA 2711420A1 CA 2711420 A CA2711420 A CA 2711420A CA 2711420 A CA2711420 A CA 2711420A CA 2711420 A1 CA2711420 A1 CA 2711420A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- oxolup
- beta
- oic acid
- acetamide
- 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
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 238000000034 method Methods 0.000 claims abstract description 96
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 4
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 557
- 239000002253 acid Substances 0.000 claims description 541
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 278
- -1 methylsucci nyl Chemical group 0.000 claims description 89
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 239000003443 antiviral agent Substances 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 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 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 12
- 108010019625 Atazanavir Sulfate Proteins 0.000 claims description 11
- 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 claims description 11
- 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 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 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 11
- 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 claims description 11
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims description 9
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 9
- 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 9
- 229960004748 abacavir Drugs 0.000 claims description 9
- 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 9
- 229960003277 atazanavir Drugs 0.000 claims description 9
- 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 9
- 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 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229960002555 zidovudine Drugs 0.000 claims description 9
- 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 8
- 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 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 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 claims description 7
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims description 7
- 229960001830 amprenavir Drugs 0.000 claims description 7
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir 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]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 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 7
- 229960003586 elvitegravir Drugs 0.000 claims description 7
- JUZYLCPPVHEVSV-LJQANCHMSA-N elvitegravir Chemical compound COC1=CC=2N([C@H](CO)C(C)C)C=C(C(O)=O)C(=O)C=2C=C1CC1=CC=CC(Cl)=C1F JUZYLCPPVHEVSV-LJQANCHMSA-N 0.000 claims description 7
- 229960000366 emtricitabine Drugs 0.000 claims description 7
- 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 claims description 7
- PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims description 7
- 229960001852 saquinavir Drugs 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- GWNOTCOIYUNTQP-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 GWNOTCOIYUNTQP-FQLXRVMXSA-N 0.000 claims description 6
- HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims description 6
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 6
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 claims 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 claims description 6
- JORVRJNILJXMMG-OLNQLETPSA-N brecanavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2OCOC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C(C=C1)=CC=C1OCC1=CSC(C)=N1 JORVRJNILJXMMG-OLNQLETPSA-N 0.000 claims description 6
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- MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 claims description 6
- SXESBRNYONQKLV-UHFFFAOYSA-N n-piperidin-1-ylacetamide Chemical compound CC(=O)NN1CCCCC1 SXESBRNYONQKLV-UHFFFAOYSA-N 0.000 claims description 6
- UKKHWKNEQBGLMI-UHFFFAOYSA-N n-pyrimidin-2-ylacetamide Chemical compound CC(=O)NC1=NC=CC=N1 UKKHWKNEQBGLMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims description 5
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- ZFGBMHRZOXDABF-UHFFFAOYSA-N n-(1,1,1-trifluoropropan-2-yl)acetamide Chemical compound FC(F)(F)C(C)NC(C)=O ZFGBMHRZOXDABF-UHFFFAOYSA-N 0.000 claims description 5
- KXOXSUKAXXZBJE-UHFFFAOYSA-N n-(1,3-dihydroisoindol-2-yl)acetamide Chemical compound C1=CC=C2CN(NC(=O)C)CC2=C1 KXOXSUKAXXZBJE-UHFFFAOYSA-N 0.000 claims description 5
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- VLGVCSRAGGWVSA-UHFFFAOYSA-N n-(2-phenylpropan-2-yl)acetamide Chemical compound CC(=O)NC(C)(C)C1=CC=CC=C1 VLGVCSRAGGWVSA-UHFFFAOYSA-N 0.000 claims description 5
- KPMQAWIAVZLFEL-UHFFFAOYSA-N n-(4-methylpiperazin-1-yl)acetamide Chemical compound CN1CCN(NC(C)=O)CC1 KPMQAWIAVZLFEL-UHFFFAOYSA-N 0.000 claims description 5
- CUZMPWBGWFGXMO-UHFFFAOYSA-N n-(4-methylpyrimidin-2-yl)acetamide Chemical compound CC(=O)NC1=NC=CC(C)=N1 CUZMPWBGWFGXMO-UHFFFAOYSA-N 0.000 claims description 5
- CUYZUESBPHQWRI-UHFFFAOYSA-N n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound CC(=O)NC=1C=C(C)ON=1 CUYZUESBPHQWRI-UHFFFAOYSA-N 0.000 claims description 5
- GDQTVPUAZAECHX-UHFFFAOYSA-N n-(cyclopropylmethyl)acetamide Chemical compound CC(=O)NCC1CC1 GDQTVPUAZAECHX-UHFFFAOYSA-N 0.000 claims description 5
- YUSMWODGNWPEBC-UHFFFAOYSA-N n-morpholin-4-ylacetamide Chemical compound CC(=O)NN1CCOCC1 YUSMWODGNWPEBC-UHFFFAOYSA-N 0.000 claims description 5
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Classifications
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- 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
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
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- 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
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
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- General Chemical & Material Sciences (AREA)
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- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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US1876608P | 2008-01-03 | 2008-01-03 | |
US61/018,766 | 2008-01-03 | ||
US3968008P | 2008-03-26 | 2008-03-26 | |
US61/039,680 | 2008-03-26 | ||
PCT/CA2008/002290 WO2009082818A1 (en) | 2008-01-03 | 2008-12-23 | Novel c-21-keto lupane derivatives preparation and use thereof |
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CA2711420A1 true CA2711420A1 (en) | 2009-07-09 |
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CA2711420A Abandoned CA2711420A1 (en) | 2008-01-03 | 2008-12-23 | Novel c-21-keto lupane derivatives preparation and use thereof |
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EP (1) | EP2240504A1 (es) |
JP (1) | JP2011508747A (es) |
CN (1) | CN101977924A (es) |
AU (1) | AU2008342536A1 (es) |
CA (1) | CA2711420A1 (es) |
MX (1) | MX2010007374A (es) |
WO (1) | WO2009082818A1 (es) |
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---|---|---|---|---|
CN105055432A (zh) * | 2008-01-25 | 2015-11-18 | 奇默里克斯公司 | 治疗病毒感染的方法 |
US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
PE20160180A1 (es) | 2010-01-27 | 2016-05-04 | Viiv Healthcare Co | Combinaciones de compuestos que comprenden inhibidores de la integrasa de vih y otros agentes terapeuticos. |
MX2012009319A (es) * | 2010-02-11 | 2012-09-12 | Glaxosmithkline Llc | Derivados de betulina. |
DK2534150T3 (en) | 2010-02-12 | 2017-06-12 | Chimerix Inc | METHODS OF TREATING VIRUS INFECTION |
WO2011139709A2 (en) | 2010-04-26 | 2011-11-10 | Chimerix, Inc. | Methods of treating retroviral infections and related dosage regimes |
WO2013020245A1 (en) * | 2011-08-08 | 2013-02-14 | Glaxosmithkline Llc | Carbonyl derivatives of betulin |
JO3387B1 (ar) | 2011-12-16 | 2019-03-13 | Glaxosmithkline Llc | مشتقات بيتولين |
CN104844679B (zh) * | 2011-12-16 | 2017-03-01 | 葛兰素史克有限责任公司 | 白桦脂醇的衍生物 |
CN103242413B (zh) | 2012-02-08 | 2015-08-26 | 江西青峰药业有限公司 | Lupane三萜系衍生物及其药学用途 |
CN104902905A (zh) | 2012-12-14 | 2015-09-09 | 葛兰素史克有限责任公司 | 药物组合物 |
US9637516B2 (en) | 2012-12-31 | 2017-05-02 | Hetero Research Foundation | Betulinic acid proline derivatives as HIV inhibitors |
US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
WO2016046786A1 (en) | 2014-09-26 | 2016-03-31 | Glaxosmithkline Intellectual Property (No.2) Limited | Long acting pharmaceutical compositions |
MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
US10370405B2 (en) * | 2015-03-16 | 2019-08-06 | Hetero Labs Limited | C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors |
WO2017115329A1 (en) * | 2015-12-30 | 2017-07-06 | Hetero Research Foundation | C-3 novel triterpenone derivatives as hiv inhibitors |
US11116737B1 (en) | 2020-04-10 | 2021-09-14 | University Of Georgia Research Foundation, Inc. | Methods of using probenecid for treatment of coronavirus infections |
-
2008
- 2008-12-23 MX MX2010007374A patent/MX2010007374A/es not_active Application Discontinuation
- 2008-12-23 WO PCT/CA2008/002290 patent/WO2009082818A1/en active Application Filing
- 2008-12-23 EP EP08867782A patent/EP2240504A1/en not_active Withdrawn
- 2008-12-23 AU AU2008342536A patent/AU2008342536A1/en not_active Abandoned
- 2008-12-23 CN CN2008801275023A patent/CN101977924A/zh active Pending
- 2008-12-23 CA CA2711420A patent/CA2711420A1/en not_active Abandoned
- 2008-12-23 JP JP2010540996A patent/JP2011508747A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
WO2009082818A8 (en) | 2009-09-03 |
EP2240504A1 (en) | 2010-10-20 |
JP2011508747A (ja) | 2011-03-17 |
WO2009082818A1 (en) | 2009-07-09 |
CN101977924A (zh) | 2011-02-16 |
AU2008342536A1 (en) | 2009-07-09 |
MX2010007374A (es) | 2010-10-05 |
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