CA2826257A1 - C-28 amines of c-3 modified betulinic acid derivatives as hiv maturation inhibitors - Google Patents

Info

Publication number

CA2826257A1

CA2826257A1 CA2826257A CA2826257A CA2826257A1 CA 2826257 A1 CA2826257 A1 CA 2826257A1 CA 2826257 A CA2826257 A CA 2826257A CA 2826257 A CA2826257 A CA 2826257A CA 2826257 A1 CA2826257 A1 CA 2826257A1

Authority

CA

Canada

Prior art keywords

alkyl

group

methyl

chrysen

cyclopenta

Prior art date

2011-01-31

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001412 amines Chemical class 0.000 title abstract description 242
• 239000003112 inhibitor Substances 0.000 title abstract description 36
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title abstract description 14
• 230000035800 maturation Effects 0.000 title abstract description 11
• 238000000034 method Methods 0.000 claims abstract description 399
• 150000001875 compounds Chemical class 0.000 claims abstract description 284
• 208000030507 AIDS Diseases 0.000 claims abstract description 85
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 12
• -1 -hydroxyl Chemical group 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 87
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000001475 halogen functional group Chemical group 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 239000003443 antiviral agent Substances 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
• 208000015181 infectious disease Diseases 0.000 claims description 7
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 6
• 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
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 4
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000003107 substituted aryl 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
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
• 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
• 239000003814 drug Substances 0.000 abstract description 15
• 229940079593 drug Drugs 0.000 abstract description 12
• 238000002360 preparation method Methods 0.000 description 267
• 229910052739 hydrogen Inorganic materials 0.000 description 244
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 242
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 235
• 238000005160 1H NMR spectroscopy Methods 0.000 description 198
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 169
• 239000000203 mixture Substances 0.000 description 163
• 239000000243 solution Substances 0.000 description 150
• 239000000376 reactant Substances 0.000 description 145
• 239000007787 solid Substances 0.000 description 145
• 239000000047 product Substances 0.000 description 129
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 97
• 235000010233 benzoic acid Nutrition 0.000 description 89
• 230000015572 biosynthetic process Effects 0.000 description 87
• 230000007062 hydrolysis Effects 0.000 description 80
• 238000006460 hydrolysis reaction Methods 0.000 description 80
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 75
• 239000005711 Benzoic acid Substances 0.000 description 73
• 238000004949 mass spectrometry Methods 0.000 description 71
• 239000002904 solvent Substances 0.000 description 67
• 208000031886 HIV Infections Diseases 0.000 description 60
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 60
• 208000037357 HIV infectious disease Diseases 0.000 description 59
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 59
• 150000001408 amides Chemical class 0.000 description 58
• 230000002829 reductive effect Effects 0.000 description 57
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 55
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 52
• 239000012043 crude product Substances 0.000 description 49
• 238000004128 high performance liquid chromatography Methods 0.000 description 46
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
• 238000000746 purification Methods 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
• 239000012044 organic layer Substances 0.000 description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 29
• 235000011054 acetic acid Nutrition 0.000 description 28
• 239000000706 filtrate Substances 0.000 description 28
• 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
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
• 239000011541 reaction mixture Substances 0.000 description 27
• 229910052938 sodium sulfate Inorganic materials 0.000 description 27
• 235000011152 sodium sulphate Nutrition 0.000 description 27
• 125000006308 propyl amino group Chemical group 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 238000001914 filtration Methods 0.000 description 24
• 239000000463 material Substances 0.000 description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
• 229960002555 zidovudine Drugs 0.000 description 23
• 150000001299 aldehydes Chemical group 0.000 description 22
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• 239000002274 desiccant Substances 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• 238000004293 19F NMR spectroscopy Methods 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 238000005903 acid hydrolysis reaction Methods 0.000 description 20
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 19
• 238000010511 deprotection reaction Methods 0.000 description 19
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 235000017557 sodium bicarbonate Nutrition 0.000 description 18
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
• 150000001559 benzoic acids Chemical class 0.000 description 17
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 16
• 239000006260 foam Substances 0.000 description 16
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 14
• 239000007832 Na2SO4 Substances 0.000 description 14
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
• PDLNHDSYGLTYDS-UHFFFAOYSA-N 3-aminopropanoic acid;hydrochloride Chemical compound Cl.NCCC(O)=O PDLNHDSYGLTYDS-UHFFFAOYSA-N 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 13
• 238000003818 flash chromatography Methods 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• 239000007821 HATU Substances 0.000 description 11
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 11
• 125000003545 alkoxy group Chemical group 0.000 description 11
• 239000013058 crude material Substances 0.000 description 11
• 150000004702 methyl esters Chemical class 0.000 description 11
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 10
• 239000005695 Ammonium acetate Substances 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
• 239000002253 acid Substances 0.000 description 10
• 235000019257 ammonium acetate Nutrition 0.000 description 10
• 229940043376 ammonium acetate Drugs 0.000 description 10
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 102100034343 Integrase Human genes 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 238000006268 reductive amination reaction Methods 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 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
• 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 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 8
• FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000011161 development Methods 0.000 description 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 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 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
• 229940095102 methyl benzoate Drugs 0.000 description 7
• 239000002777 nucleoside Substances 0.000 description 7
• 150000003833 nucleoside derivatives Chemical class 0.000 description 7
• 238000002953 preparative HPLC Methods 0.000 description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
• 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 7
• 150000003512 tertiary amines Chemical class 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• 108010019625 Atazanavir Sulfate Proteins 0.000 description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
• 108010010369 HIV Protease Proteins 0.000 description 6
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
• 108010002350 Interleukin-2 Proteins 0.000 description 6
• 102000000588 Interleukin-2 Human genes 0.000 description 6
• 208000007766 Kaposi sarcoma Diseases 0.000 description 6
• 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 6
• 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 description 6
• 108700017836 Prophet of Pit-1 Proteins 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
• 238000006069 Suzuki reaction reaction Methods 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
• 239000002585 base Substances 0.000 description 6
• 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 description 6
• 210000000234 capsid Anatomy 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 125000004093 cyano group Chemical group *C#N 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 6
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 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
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 5
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 5
• FSRMWCVZAUEPEQ-UHFFFAOYSA-N 3-(1,1-dioxo-1,4-thiazinan-4-yl)propan-1-amine Chemical compound NCCCN1CCS(=O)(=O)CC1 FSRMWCVZAUEPEQ-UHFFFAOYSA-N 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
• 229940126656 GS-4224 Drugs 0.000 description 5
• 108060001084 Luciferase Proteins 0.000 description 5
• 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
• 229960004748 abacavir Drugs 0.000 description 5
• 208000001763 cytomegalovirus retinitis Diseases 0.000 description 5
• 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 description 5
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