CA2900124A1 - C-19 modified triterpenoids with hiv maturation inhibitory activity - Google Patents
C-19 modified triterpenoids with hiv maturation inhibitory activity Download PDFInfo
- Publication number
- CA2900124A1 CA2900124A1 CA2900124A CA2900124A CA2900124A1 CA 2900124 A1 CA2900124 A1 CA 2900124A1 CA 2900124 A CA2900124 A CA 2900124A CA 2900124 A CA2900124 A CA 2900124A CA 2900124 A1 CA2900124 A1 CA 2900124A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- mmol
- cyclopenta
- octadecahydro
- 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
- 230000035800 maturation Effects 0.000 title abstract description 13
- 150000003648 triterpenes Chemical class 0.000 title abstract description 6
- 230000002401 inhibitory effect Effects 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 307
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 208000030507 AIDS Diseases 0.000 claims abstract description 86
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- -1 -hydroxyl Chemical group 0.000 claims description 70
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000003443 antiviral agent Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000002835 hiv fusion inhibitor Substances 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 229960005475 antiinfective agent Drugs 0.000 claims description 7
- 239000002955 immunomodulating agent Substances 0.000 claims description 7
- 229940121354 immunomodulator Drugs 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 239000004599 antimicrobial Substances 0.000 claims description 4
- 230000002584 immunomodulator Effects 0.000 claims description 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 abstract description 34
- 239000003814 drug Substances 0.000 abstract description 15
- 229940079593 drug Drugs 0.000 abstract description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 437
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 286
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 246
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 211
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 198
- 238000002360 preparation method Methods 0.000 description 192
- 238000002953 preparative HPLC Methods 0.000 description 192
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 171
- 229910001868 water Inorganic materials 0.000 description 167
- 239000000047 product Substances 0.000 description 151
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 147
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 147
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 230000002829 reductive effect Effects 0.000 description 133
- 239000007787 solid Substances 0.000 description 130
- 238000005160 1H NMR spectroscopy Methods 0.000 description 119
- 239000000243 solution Substances 0.000 description 114
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 109
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 92
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 92
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
- 239000012071 phase Substances 0.000 description 74
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 70
- 229910052739 hydrogen Inorganic materials 0.000 description 68
- 239000002904 solvent Substances 0.000 description 68
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 63
- 230000002441 reversible effect Effects 0.000 description 62
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 62
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 60
- 208000031886 HIV Infections Diseases 0.000 description 60
- 208000037357 HIV infectious disease Diseases 0.000 description 59
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 59
- 239000011541 reaction mixture Substances 0.000 description 58
- 229910052757 nitrogen Inorganic materials 0.000 description 53
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 40
- 239000004810 polytetrafluoroethylene Substances 0.000 description 40
- 238000003756 stirring Methods 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 239000000843 powder Substances 0.000 description 39
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 35
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
- 229910052938 sodium sulfate Inorganic materials 0.000 description 34
- 235000011152 sodium sulphate Nutrition 0.000 description 34
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 29
- 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 26
- 239000006260 foam Substances 0.000 description 26
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 24
- 239000005695 Ammonium acetate Substances 0.000 description 24
- 235000019257 ammonium acetate Nutrition 0.000 description 24
- 229940043376 ammonium acetate Drugs 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 23
- 238000000746 purification Methods 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 239000003643 water by type Substances 0.000 description 23
- 229960002555 zidovudine Drugs 0.000 description 23
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 22
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 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 21
- 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 20
- 239000000725 suspension Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 19
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 17
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 238000010828 elution Methods 0.000 description 13
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 11
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 11
- 235000011054 acetic acid Nutrition 0.000 description 11
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000012258 stirred mixture Substances 0.000 description 11
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 11
- 102100034343 Integrase Human genes 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000012043 crude product Substances 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
- 238000010438 heat treatment Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 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
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 9
- 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 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 9
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 8
- 239000005711 Benzoic acid Substances 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
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- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 8
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- 125000003545 alkoxy group Chemical group 0.000 description 8
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- 238000011161 development Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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- 238000005481 NMR spectroscopy Methods 0.000 description 7
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
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- 239000002777 nucleoside Substances 0.000 description 7
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- XTYSXGHMTNTKFH-BDEHJDMKSA-N (2s)-1-[(2s,4r)-4-benzyl-2-hydroxy-5-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-5-oxopentyl]-n-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide;hydrate Chemical compound O.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 XTYSXGHMTNTKFH-BDEHJDMKSA-N 0.000 description 6
- 108010019625 Atazanavir Sulfate Proteins 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000007821 HATU Substances 0.000 description 6
- 108010010369 HIV Protease Proteins 0.000 description 6
- 102000000588 Interleukin-2 Human genes 0.000 description 6
- 108010002350 Interleukin-2 Proteins 0.000 description 6
- 208000007766 Kaposi sarcoma Diseases 0.000 description 6
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- SGOIRFVFHAKUTI-ZCFIWIBFSA-N tenofovir (anhydrous) Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(O)=O)C=NC2=C1N SGOIRFVFHAKUTI-ZCFIWIBFSA-N 0.000 description 1
- JFVZFKDSXNQEJW-CQSZACIVSA-N tenofovir disoproxil Chemical compound N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N JFVZFKDSXNQEJW-CQSZACIVSA-N 0.000 description 1
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- 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
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361761403P | 2013-02-06 | 2013-02-06 | |
| US61/761,403 | 2013-02-06 | ||
| PCT/US2014/014647 WO2014123889A1 (en) | 2013-02-06 | 2014-02-04 | C-19 modified triterpenoids with hiv maturation inhibitory activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2900124A1 true CA2900124A1 (en) | 2014-08-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2900124A Abandoned CA2900124A1 (en) | 2013-02-06 | 2014-02-04 | C-19 modified triterpenoids with hiv maturation inhibitory activity |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20140221361A1 (enExample) |
| EP (1) | EP2953960A1 (enExample) |
| JP (1) | JP6186010B2 (enExample) |
| KR (1) | KR20150115881A (enExample) |
| CN (1) | CN105121454A (enExample) |
| AR (1) | AR094684A1 (enExample) |
| AU (1) | AU2014215468B2 (enExample) |
| BR (1) | BR112015018491A2 (enExample) |
| CA (1) | CA2900124A1 (enExample) |
| EA (1) | EA027371B1 (enExample) |
| IL (1) | IL240289A0 (enExample) |
| MX (1) | MX2015010003A (enExample) |
| SG (1) | SG11201505639SA (enExample) |
| TW (1) | TW201443073A (enExample) |
| WO (1) | WO2014123889A1 (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 |
| 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 |
| WO2017025901A1 (en) * | 2015-08-11 | 2017-02-16 | Hetero Research Foundation | Novel c28-analogues with c3-modifications of triterpene derivatives as hiv inhibitors |
| US20180273579A1 (en) | 2015-09-24 | 2018-09-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Compounds with hiv maturation inhibitory activity |
| WO2017125870A1 (en) | 2016-01-20 | 2017-07-27 | 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 |
| WO2017149518A1 (en) * | 2016-03-04 | 2017-09-08 | Hetero Labs Limited | C-3 novel triterpene with c-17 amine derivatives as hiv inhibitors |
| PT3478662T (pt) * | 2016-06-30 | 2020-12-09 | Viiv Healthcare Uk No 5 Ltd | Derivados de azadecalina como inibidores da replicação do vírus da imunodeficiência humana |
| WO2018044853A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Conpany | Combinations and uses and treatments thereof |
| WO2018044852A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| US20210347813A1 (en) | 2018-04-24 | 2021-11-11 | Viiv Healthcare Uk (No. 5) Limited | Compounds with hiv maturation inhibitory activity |
| EP3796900A4 (en) * | 2018-06-29 | 2022-03-30 | DFH Therapeutics | TRITERPEN AMINE DERIVATIVES |
| CA3129743A1 (en) | 2019-02-11 | 2020-08-20 | Hetero Labs Limited | Novel triterpene derivatives as hiv inhibitors |
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| JP2694048B2 (ja) * | 1991-05-09 | 1997-12-24 | 日立建機株式会社 | 建設機械の油圧駆動装置 |
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
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| EA023578B1 (ru) * | 2011-01-31 | 2016-06-30 | Бристол-Маерс Сквибб Компани | C28-амины c3-модифицированных производных бетулиновой кислоты в качестве ингибиторов созревания вич |
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-
2014
- 2014-02-04 US US14/172,389 patent/US20140221361A1/en not_active Abandoned
- 2014-02-04 BR BR112015018491A patent/BR112015018491A2/pt not_active Application Discontinuation
- 2014-02-04 JP JP2015556998A patent/JP6186010B2/ja not_active Expired - Fee Related
- 2014-02-04 CN CN201480019576.0A patent/CN105121454A/zh active Pending
- 2014-02-04 KR KR1020157023907A patent/KR20150115881A/ko not_active Withdrawn
- 2014-02-04 SG SG11201505639SA patent/SG11201505639SA/en unknown
- 2014-02-04 EA EA201591406A patent/EA027371B1/ru not_active IP Right Cessation
- 2014-02-04 EP EP14705662.6A patent/EP2953960A1/en not_active Withdrawn
- 2014-02-04 CA CA2900124A patent/CA2900124A1/en not_active Abandoned
- 2014-02-04 MX MX2015010003A patent/MX2015010003A/es unknown
- 2014-02-04 AU AU2014215468A patent/AU2014215468B2/en not_active Ceased
- 2014-02-04 WO PCT/US2014/014647 patent/WO2014123889A1/en not_active Ceased
- 2014-02-05 TW TW103103839A patent/TW201443073A/zh unknown
- 2014-02-06 AR ARP140100400A patent/AR094684A1/es unknown
-
2015
- 2015-08-02 IL IL240289A patent/IL240289A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP6186010B2 (ja) | 2017-08-23 |
| EA201591406A1 (ru) | 2015-12-30 |
| WO2014123889A1 (en) | 2014-08-14 |
| EP2953960A1 (en) | 2015-12-16 |
| KR20150115881A (ko) | 2015-10-14 |
| SG11201505639SA (en) | 2015-08-28 |
| IL240289A0 (en) | 2015-09-24 |
| US20140221361A1 (en) | 2014-08-07 |
| AU2014215468B2 (en) | 2017-05-18 |
| BR112015018491A2 (pt) | 2017-07-18 |
| TW201443073A (zh) | 2014-11-16 |
| CN105121454A (zh) | 2015-12-02 |
| JP2016507558A (ja) | 2016-03-10 |
| MX2015010003A (es) | 2015-10-30 |
| AR094684A1 (es) | 2015-08-19 |
| AU2014215468A1 (en) | 2015-09-24 |
| EA027371B1 (ru) | 2017-07-31 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20170203 |
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| FZDE | Discontinued |
Effective date: 20190801 |