CA2718950A1 - Bridged heterocycles as hiv integrase inhibitors - Google Patents

Info

Publication number

CA2718950A1

CA2718950A1 CA2718950A CA2718950A CA2718950A1 CA 2718950 A1 CA2718950 A1 CA 2718950A1 CA 2718950 A CA2718950 A CA 2718950A CA 2718950 A CA2718950 A CA 2718950A CA 2718950 A1 CA2718950 A1 CA 2718950A1

Authority

CA

Canada

Prior art keywords

alkyl

mmol

hydroxy

alkoxy

methyl

Prior art date

2008-03-19

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

• 229940099797 HIV integrase inhibitor Drugs 0.000 title claims description 14
• 239000003084 hiv integrase inhibitor Substances 0.000 title claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 246
• 208000030507 AIDS Diseases 0.000 claims abstract description 91
• 238000000034 method Methods 0.000 claims abstract description 79
• 208000031886 HIV Infections Diseases 0.000 claims abstract description 65
• 208000037357 HIV infectious disease Diseases 0.000 claims abstract description 64
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 64
• 150000003839 salts Chemical class 0.000 claims abstract description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 308
• 125000000217 alkyl group Chemical group 0.000 claims description 200
• 239000000203 mixture Substances 0.000 claims description 198
• -1 diphenylalkyl Chemical group 0.000 claims description 162
• 125000003545 alkoxy group Chemical group 0.000 claims description 88
• 239000001257 hydrogen Substances 0.000 claims description 83
• 125000001188 haloalkyl group Chemical group 0.000 claims description 57
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 56
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 239000003112 inhibitor Substances 0.000 claims description 49
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 43
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 239000003795 chemical substances by application Substances 0.000 claims description 32
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000001425 triazolyl group Chemical group 0.000 claims description 25
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 21
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 239000002777 nucleoside Substances 0.000 claims description 19
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000002883 imidazolyl group Chemical group 0.000 claims description 17
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 15
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 15
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 15
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 15
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 13
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 13
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
• 125000000335 thiazolyl group Chemical group 0.000 claims description 13
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 12
• 125000002393 azetidinyl group Chemical group 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 12
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 9
• 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 9
• 230000034303 cell budding Effects 0.000 claims description 9
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 9
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 9
• 230000035800 maturation Effects 0.000 claims description 9
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 8
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 5
• 101100134925 Gallus gallus COR6 gene Chemical group 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 101100203602 Hypocrea jecorina (strain QM6a) sor7 gene Proteins 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 22
• 125000001475 halogen functional group Chemical group 0.000 claims 19
• BRUBMWOBZYQCTE-UHFFFAOYSA-N 3,7-diazatricyclo[8.2.1.02,7]trideca-1(12),2,4,8,10-pentaene-4-carboxamide Chemical compound C12=NC(C(=O)N)=CCN2C=CC2=CC=C1C2 BRUBMWOBZYQCTE-UHFFFAOYSA-N 0.000 claims 3
• 230000001225 therapeutic effect Effects 0.000 claims 1
• 230000003612 virological effect Effects 0.000 abstract description 11
• 108010002459 HIV Integrase Proteins 0.000 abstract description 8
• 230000010354 integration Effects 0.000 abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
• 230000009471 action Effects 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 457
• 239000000543 intermediate Substances 0.000 description 229
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 170
• 235000019439 ethyl acetate Nutrition 0.000 description 153
• 239000000243 solution Substances 0.000 description 151
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 145
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 145
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 143
• 101150041968 CDC13 gene Proteins 0.000 description 138
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 111
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 107
• 229910001868 water Inorganic materials 0.000 description 102
• 239000011541 reaction mixture Substances 0.000 description 94
• 238000005160 1H NMR spectroscopy Methods 0.000 description 93
• 239000003921 oil Substances 0.000 description 83
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 72
• 229910052938 sodium sulfate Inorganic materials 0.000 description 72
• 235000011152 sodium sulphate Nutrition 0.000 description 72
• 239000007832 Na2SO4 Substances 0.000 description 71
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 69
• 239000007787 solid Substances 0.000 description 69
• 238000005481 NMR spectroscopy Methods 0.000 description 62
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
• 239000012267 brine Substances 0.000 description 56
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 56
• 238000003818 flash chromatography Methods 0.000 description 49
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 48
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
• 230000000694 effects Effects 0.000 description 36
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
• 241000725303 Human immunodeficiency virus Species 0.000 description 34
• 150000002431 hydrogen Chemical group 0.000 description 34
• 235000019341 magnesium sulphate Nutrition 0.000 description 34
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 31
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 29
• 238000004128 high performance liquid chromatography Methods 0.000 description 29
• 239000000741 silica gel Substances 0.000 description 29
• 229910002027 silica gel Inorganic materials 0.000 description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• 239000013058 crude material Substances 0.000 description 28
• 239000010410 layer Substances 0.000 description 28
• 230000002829 reductive effect Effects 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
• 230000015572 biosynthetic process Effects 0.000 description 25
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
• 239000003814 drug Substances 0.000 description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
• 235000017557 sodium bicarbonate Nutrition 0.000 description 22
• 229910000027 potassium carbonate Inorganic materials 0.000 description 21
• 239000000706 filtrate Substances 0.000 description 20
• 125000005843 halogen group Chemical group 0.000 description 20
• 230000014759 maintenance of location Effects 0.000 description 20
• 238000003786 synthesis reaction Methods 0.000 description 20
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 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 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 17
• 229940079593 drug Drugs 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 17
• 229960002555 zidovudine Drugs 0.000 description 17
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 15
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 15
• 239000000284 extract Substances 0.000 description 15
• 238000001914 filtration Methods 0.000 description 15
• 238000000338 in vitro Methods 0.000 description 15
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 15
• 235000015320 potassium carbonate Nutrition 0.000 description 14
• 238000002953 preparative HPLC Methods 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 13
• 230000000840 anti-viral effect Effects 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 13
• 239000011368 organic material Substances 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• 239000008096 xylene Substances 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 12
• 241000700605 Viruses Species 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• 229910000029 sodium carbonate Inorganic materials 0.000 description 11
• 235000017550 sodium carbonate Nutrition 0.000 description 11
• 208000007766 Kaposi sarcoma Diseases 0.000 description 10
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 9
• 239000006260 foam Substances 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• KCIUWHKNKKYAPE-UHFFFAOYSA-N 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4h-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid Chemical compound OC(=O)C=1N=C2N(CC3)CCC3CN2C(=O)C=1OCC1=CC=CC=C1 KCIUWHKNKKYAPE-UHFFFAOYSA-N 0.000 description 8
• 102100034343 Integrase Human genes 0.000 description 8
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 229910052681 coesite Inorganic materials 0.000 description 8
• 239000012230 colorless oil Substances 0.000 description 8
• 229910052906 cristobalite Inorganic materials 0.000 description 8
• 239000010779 crude oil Substances 0.000 description 8
• 125000004494 ethyl ester group Chemical group 0.000 description 8
• 239000012280 lithium aluminium hydride Substances 0.000 description 8
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 8
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 229910052682 stishovite Inorganic materials 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• 229910052905 tridymite Inorganic materials 0.000 description 8
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• SOSFYCQTXQIGFF-UHFFFAOYSA-N 2,6-diazatricyclo[6.2.2.02,7]dodeca-1(10),4,6,8-tetraene-5-carboxamide Chemical compound C1=C(CC2)C3=NC(C(=O)N)=CCN3C2=C1 SOSFYCQTXQIGFF-UHFFFAOYSA-N 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
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• 239000007821 HATU Substances 0.000 description 7
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 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
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 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 7
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• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• 108010019625 Atazanavir Sulfate Proteins 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
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• 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
• 229960004748 abacavir Drugs 0.000 description 6
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
• 230000002378 acidificating effect Effects 0.000 description 6
• 235000011114 ammonium hydroxide Nutrition 0.000 description 6
• 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 6
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• BMPSHOYVCUTFLJ-UHFFFAOYSA-N ethyl 5-benzoyloxy-2-[1-(2-benzoyloxyethoxy)-4-(methylsulfonyloxymethyl)cyclohexyl]-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound CCOC(=O)C=1N=C(C2(CCC(COS(C)(=O)=O)CC2)OCCOC(=O)C=2C=CC=CC=2)NC(=O)C=1OC(=O)C1=CC=CC=C1 BMPSHOYVCUTFLJ-UHFFFAOYSA-N 0.000 description 1
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