JP5902704B2 - Ｈｉｖ複製の阻害剤 - Google Patents

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Publication number

JP5902704B2

JP5902704B2 JP2013538301A JP2013538301A JP5902704B2 JP 5902704 B2 JP5902704 B2 JP 5902704B2 JP 2013538301 A JP2013538301 A JP 2013538301A JP 2013538301 A JP2013538301 A JP 2013538301A JP 5902704 B2 JP5902704 B2 JP 5902704B2

Authority

JP

Japan

Prior art keywords

methyl

mmol

tetrahydro

compound

compounds

Prior art date

2010-11-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title description 20
• 230000010076 replication Effects 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 217
• 239000000203 mixture Substances 0.000 claims description 101
• 238000002360 preparation method Methods 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 43
• 239000003814 drug Substances 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• 229940079593 drug Drugs 0.000 claims description 16
• 208000031886 HIV Infections Diseases 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 208000037357 HIV infectious disease Diseases 0.000 claims description 11
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 239000013543 active substance Substances 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
• 239000007787 solid Substances 0.000 description 84
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
• 238000006243 chemical reaction Methods 0.000 description 63
• 239000000243 solution Substances 0.000 description 62
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• -1 cansylate Chemical compound 0.000 description 53
• 235000019439 ethyl acetate Nutrition 0.000 description 50
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 46
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 238000005481 NMR spectroscopy Methods 0.000 description 35
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
• 239000010410 layer Substances 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 239000012044 organic layer Substances 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 230000002378 acidificating effect Effects 0.000 description 25
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• 238000001914 filtration Methods 0.000 description 19
• 238000003818 flash chromatography Methods 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
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• 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 15
• 230000003993 interaction Effects 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 239000003826 tablet Substances 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 125000005336 allyloxy group Chemical group 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 239000007788 liquid Substances 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
• 241000124008 Mammalia Species 0.000 description 11
• 239000002552 dosage form Substances 0.000 description 11
• 239000012065 filter cake Substances 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 239000002253 acid Substances 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 8
• 239000012071 phase Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 239000012453 solvate Substances 0.000 description 7
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 230000008859 change Effects 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 239000011928 denatured alcohol Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 150000004677 hydrates Chemical class 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• NOGJZOSEZHFDPM-INIZCTEOSA-N methyl (2s)-2-(4-iodo-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridin-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate Chemical compound C1CCCC2=C1SC1=NC(C)=C([C@H](OC(C)(C)C)C(=O)OC)C(I)=C12 NOGJZOSEZHFDPM-INIZCTEOSA-N 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• 150000001298 alcohols Chemical class 0.000 description 5
• 229910052786 argon Inorganic materials 0.000 description 5
• 239000010408 film Substances 0.000 description 5
• 230000014759 maintenance of location Effects 0.000 description 5
• 239000002245 particle Substances 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 4
• 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• 239000002202 Polyethylene glycol Substances 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 241000700605 Viruses Species 0.000 description 4
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
• 239000012346 acetyl chloride Substances 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 108010005774 beta-Galactosidase Proteins 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 231100000135 cytotoxicity Toxicity 0.000 description 4
• 230000003013 cytotoxicity Effects 0.000 description 4
• 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 4
• 230000003111 delayed effect Effects 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000011067 equilibration Methods 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 239000000796 flavoring agent Substances 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 230000001965 increasing effect Effects 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
• 229920001223 polyethylene glycol Polymers 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000002243 precursor Substances 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 230000000541 pulsatile effect Effects 0.000 description 4
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
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• 239000011593 sulfur Substances 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 230000002459 sustained effect Effects 0.000 description 4
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
• XBNRJKSGOLRSRX-UHFFFAOYSA-N (4-chloro-2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1O XBNRJKSGOLRSRX-UHFFFAOYSA-N 0.000 description 3
• ZTUSRCVHZBMXQQ-UHFFFAOYSA-N 2-(4-iodo-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridin-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetic acid Chemical compound C1CCCC2=C1SC1=C2C(I)=C(C(OC(C)(C)C)C(O)=O)C(C)=N1 ZTUSRCVHZBMXQQ-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• IEMGADFFJIRSAI-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridine Chemical class S1C2=NC=CC=C2C2=C1CCCC2 IEMGADFFJIRSAI-UHFFFAOYSA-N 0.000 description 3
• 208000030507 AIDS Diseases 0.000 description 3
• UXCAQJAQSWSNPQ-XLPZGREQSA-N Alovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](F)C1 UXCAQJAQSWSNPQ-XLPZGREQSA-N 0.000 description 3
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 3
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• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 description 3
• YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 3
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• 208000035475 disorder Diseases 0.000 description 3
• QJVURSNCFOBOIZ-UHFFFAOYSA-N ethyl 4-chloro-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridine-3-carboxylate Chemical compound C1CCCC2=C1SC1=NC(C)=C(C(=O)OCC)C(Cl)=C12 QJVURSNCFOBOIZ-UHFFFAOYSA-N 0.000 description 3
• MBKMBUUQNOMKFV-UHFFFAOYSA-N ethyl 4-iodo-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridine-3-carboxylate Chemical compound C1CCCC2=C1SC1=NC(C)=C(C(=O)OCC)C(I)=C12 MBKMBUUQNOMKFV-UHFFFAOYSA-N 0.000 description 3
• 235000013355 food flavoring agent Nutrition 0.000 description 3
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• 229910021645 metal ion Inorganic materials 0.000 description 3
• NOGJZOSEZHFDPM-UHFFFAOYSA-N methyl 2-(4-iodo-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridin-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate Chemical compound C1CCCC2=C1SC1=NC(C)=C(C(OC(C)(C)C)C(=O)OC)C(I)=C12 NOGJZOSEZHFDPM-UHFFFAOYSA-N 0.000 description 3
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 3
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
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• 239000012279 sodium borohydride Substances 0.000 description 3
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• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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• BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 description 3
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• 230000003612 virological effect Effects 0.000 description 3
• JEXLMJZPIFTEMP-UHFFFAOYSA-N (2-amino-5,7-dihydro-4h-thieno[2,3-c]pyran-3-yl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=C(N)SC2=C1CCOC2 JEXLMJZPIFTEMP-UHFFFAOYSA-N 0.000 description 2
• NQYPDZJVSAZAHO-NRFANRHFSA-N (2S)-2-[4-(4-chloro-2-hydroxyphenyl)-2-methyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-b]pyridin-3-yl]-2-[(2-methylpropan-2-yl)oxy]acetic acid Chemical compound CC(C)(C)O[C@H](C(O)=O)C=1C(C)=NC=2SC=3CCCCC=3C=2C=1C1=CC=C(Cl)C=C1O NQYPDZJVSAZAHO-NRFANRHFSA-N 0.000 description 2
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