TWI628188B - 具有ｈｉｖ成熟抑制活性之ｃ－１７及ｃ－３經修飾之三萜類化合物 - Google Patents

Info

Publication number

TWI628188B

TWI628188B TW101103140A TW101103140A TWI628188B TW I628188 B TWI628188 B TW I628188B TW 101103140 A TW101103140 A TW 101103140A TW 101103140 A TW101103140 A TW 101103140A TW I628188 B TWI628188 B TW I628188B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

substituted

compound

pentamethyl

Prior art date

2011-01-31

Links

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• 230000035800 maturation Effects 0.000 title abstract description 12
• 150000003648 triterpenes Chemical class 0.000 title abstract description 4
• 230000002401 inhibitory effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 313
• 208000030507 AIDS Diseases 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 10
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 417
• -1 -C 3 -6 cycloalkyl Chemical group 0.000 claims description 401
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
• 239000003443 antiviral agent Substances 0.000 claims description 8
• 208000031886 HIV Infections Diseases 0.000 claims description 7
• 208000037357 HIV infectious disease Diseases 0.000 claims description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 229960005475 antiinfective agent Drugs 0.000 claims description 6
• 125000001475 halogen functional group Chemical group 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 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 6
• 239000004599 antimicrobial Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 230000002584 immunomodulator Effects 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
• 241000124008 Mammalia Species 0.000 claims description 3
• 229940124597 therapeutic agent Drugs 0.000 claims description 3
• 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 428
• 239000003112 inhibitor Substances 0.000 abstract description 20
• 230000004071 biological effect Effects 0.000 abstract 1
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 282
• 238000002360 preparation method Methods 0.000 description 280
• 239000000203 mixture Substances 0.000 description 238
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 237
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 230
• 229910052739 hydrogen Inorganic materials 0.000 description 213
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 184
• 239000007787 solid Substances 0.000 description 150
• 229940095102 methyl benzoate Drugs 0.000 description 141
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 132
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 126
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
• 238000002953 preparative HPLC Methods 0.000 description 121
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
• 239000000047 product Substances 0.000 description 115
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 99
• 239000012071 phase Substances 0.000 description 88
• 230000002441 reversible effect Effects 0.000 description 80
• 238000000746 purification Methods 0.000 description 78
• 230000015572 biosynthetic process Effects 0.000 description 76
• 239000002904 solvent Substances 0.000 description 73
• 150000001412 amines Chemical class 0.000 description 71
• 230000014759 maintenance of location Effects 0.000 description 68
• 239000004202 carbamide Substances 0.000 description 66
• 238000010931 ester hydrolysis Methods 0.000 description 64
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 239000000376 reactant Substances 0.000 description 56
• 239000011541 reaction mixture Substances 0.000 description 56
• 239000000243 solution Substances 0.000 description 54
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 53
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
• 235000019439 ethyl acetate Nutrition 0.000 description 49
• 230000002829 reductive effect Effects 0.000 description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 43
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 43
• 238000006243 chemical reaction Methods 0.000 description 40
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 38
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 33
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• 239000000126 substance Substances 0.000 description 22
• 125000006630 butoxycarbonylamino group Chemical group 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 21
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 20
• 239000005695 Ammonium acetate Substances 0.000 description 20
• 235000019257 ammonium acetate Nutrition 0.000 description 20
• 229940043376 ammonium acetate Drugs 0.000 description 20
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 19
• 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 18
• 238000004128 high performance liquid chromatography Methods 0.000 description 18
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 239000002168 alkylating agent Substances 0.000 description 16
• 229940100198 alkylating agent Drugs 0.000 description 16
• 238000001914 filtration Methods 0.000 description 16
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 15
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 150000001408 amides Chemical class 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• JTNKXYWGZCNBCH-UHFFFAOYSA-N 3-(dimethylamino)propanoic acid;hydron;chloride Chemical compound Cl.CN(C)CCC(O)=O JTNKXYWGZCNBCH-UHFFFAOYSA-N 0.000 description 11
• QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 description 11
• CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 description 11
• DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 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 11
• MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 description 11
• 239000002002 slurry Substances 0.000 description 11
• 239000011734 sodium Substances 0.000 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 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 239000012267 brine Substances 0.000 description 10
• 239000006227 byproduct Substances 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 10
• 230000007062 hydrolysis Effects 0.000 description 10
• 238000006460 hydrolysis reaction Methods 0.000 description 10
• MZDGXTXYHXDWIM-UHFFFAOYSA-N methyl benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=CC=C1 MZDGXTXYHXDWIM-UHFFFAOYSA-N 0.000 description 10
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 9
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 9
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 9
• 239000007789 gas Substances 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 9
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 229940038384 octadecane Drugs 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
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 229940124530 sulfonamide Drugs 0.000 description 9
• 239000005711 Benzoic acid Substances 0.000 description 8
• 235000011054 acetic acid Nutrition 0.000 description 8
• 235000010233 benzoic acid Nutrition 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 150000003141 primary amines Chemical class 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 239000011550 stock solution Substances 0.000 description 8
• 229960002555 zidovudine Drugs 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
• 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 7
• 239000007864 aqueous solution Substances 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 239000002274 desiccant Substances 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 239000006260 foam Substances 0.000 description 7
• 239000012948 isocyanate Substances 0.000 description 7
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 7
• 238000010898 silica gel chromatography Methods 0.000 description 7
• 150000003456 sulfonamides Chemical class 0.000 description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 7
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• DGFNGRBBDQUMJZ-UHFFFAOYSA-N FC(C(=O)O)(F)F.C(C1=CC=CC=C1)(=O)OC Chemical compound FC(C(=O)O)(F)F.C(C1=CC=CC=C1)(=O)OC DGFNGRBBDQUMJZ-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 125000004104 aryloxy group Chemical group 0.000 description 6
• 150000003857 carboxamides Chemical class 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 229960001936 indinavir Drugs 0.000 description 6
• 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 6
• 238000004811 liquid chromatography Methods 0.000 description 6
• 238000004949 mass spectrometry Methods 0.000 description 6
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 6
• 125000005296 thioaryloxy group Chemical group 0.000 description 6
• 125000005404 thioheteroaryloxy group Chemical group 0.000 description 6
• 150000003573 thiols Chemical class 0.000 description 6
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
• 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 5
• 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 5
• 239000007821 HATU Substances 0.000 description 5
• 229940122440 HIV protease inhibitor Drugs 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 241000700605 Viruses Species 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
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