AU2009225577A1 - Bridged heterocycles as HIV integrase inhibitors - Google Patents

Info

Publication number

AU2009225577A1

AU2009225577A1 AU2009225577A AU2009225577A AU2009225577A1 AU 2009225577 A1 AU2009225577 A1 AU 2009225577A1 AU 2009225577 A AU2009225577 A AU 2009225577A AU 2009225577 A AU2009225577 A AU 2009225577A AU 2009225577 A1 AU2009225577 A1 AU 2009225577A1

Authority

AU

Australia

Prior art keywords

alkyl

mmol

hydroxy

pct

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
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• 229940099797 HIV integrase inhibitor Drugs 0.000 title claims description 11
• 239000003084 hiv integrase inhibitor Substances 0.000 title claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 title description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 604
• 150000001875 compounds Chemical class 0.000 claims description 246
• 239000000203 mixture Substances 0.000 claims description 208
• -1 dioxothiazinyl Chemical group 0.000 claims description 174
• 125000000217 alkyl group Chemical group 0.000 claims description 167
• 208000030507 AIDS Diseases 0.000 claims description 89
• 238000000034 method Methods 0.000 claims description 78
• 125000003545 alkoxy group Chemical group 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 71
• 208000031886 HIV Infections Diseases 0.000 claims description 62
• 208000037357 HIV infectious disease Diseases 0.000 claims description 61
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 61
• 150000002431 hydrogen Chemical class 0.000 claims description 54
• 239000003112 inhibitor Substances 0.000 claims description 53
• 125000001188 haloalkyl group Chemical group 0.000 claims description 46
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 33
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 25
• 125000001425 triazolyl group Chemical group 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 21
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
• 239000002777 nucleoside Substances 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
• 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002541 furyl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 13
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000002393 azetidinyl group Chemical group 0.000 claims description 11
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 11
• 125000002971 oxazolyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 9
• 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 9
• 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 9
• 108010002459 HIV Integrase Proteins 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
• 230000035800 maturation Effects 0.000 claims description 9
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 239000004030 hiv protease inhibitor Substances 0.000 claims description 6
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 230000004927 fusion Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
• 125000001475 halogen functional group Chemical group 0.000 claims 13
• 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
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 445
• 239000000543 intermediate Substances 0.000 description 230
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 200
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 185
• 238000005481 NMR spectroscopy Methods 0.000 description 181
• 239000000243 solution Substances 0.000 description 157
• 235000019439 ethyl acetate Nutrition 0.000 description 149
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 143
• 239000007787 solid Substances 0.000 description 123
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
• 239000011541 reaction mixture Substances 0.000 description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
• 239000011734 sodium Substances 0.000 description 89
• 239000003921 oil Substances 0.000 description 83
• 238000004128 high performance liquid chromatography Methods 0.000 description 80
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
• 239000012267 brine Substances 0.000 description 58
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 58
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 53
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 238000003818 flash chromatography Methods 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
• 238000006243 chemical reaction Methods 0.000 description 42
• 241000725303 Human immunodeficiency virus Species 0.000 description 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
• 230000000694 effects Effects 0.000 description 36
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 33
• 239000002904 solvent Substances 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
• 238000005160 1H NMR spectroscopy Methods 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
• 239000013058 crude material Substances 0.000 description 29
• 239000000741 silica gel Substances 0.000 description 29
• 229910002027 silica gel Inorganic materials 0.000 description 29
• 239000010410 layer Substances 0.000 description 28
• 230000002829 reductive effect Effects 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
• 230000015572 biosynthetic process Effects 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000003814 drug Substances 0.000 description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 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
• 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
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 229940079593 drug Drugs 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 17
• 238000002953 preparative HPLC Methods 0.000 description 17
• 229960002555 zidovudine Drugs 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
• 238000001914 filtration Methods 0.000 description 16
• 239000000284 extract Substances 0.000 description 15
• 238000000338 in vitro Methods 0.000 description 15
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 14
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 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
• 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
• 239000012043 crude product Substances 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
• STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• 241000700605 Viruses Species 0.000 description 11
• 239000006260 foam Substances 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• 230000003612 virological effect Effects 0.000 description 11
• 208000007766 Kaposi sarcoma Diseases 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
• 239000007821 HATU Substances 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
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 125000004494 ethyl ester group Chemical group 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
• 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 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
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• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 8
• 229910004298 SiO 2 Inorganic materials 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
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• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• 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 7
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• 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
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 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
• 239000012280 lithium aluminium hydride Substances 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
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• BWMQGQFQSFSVKB-UHFFFAOYSA-N C1CC2CCC1CN1CC=C(C(=O)N)N=C12 Chemical compound C1CC2CCC1CN1CC=C(C(=O)N)N=C12 BWMQGQFQSFSVKB-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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• 230000002378 acidificating effect Effects 0.000 description 6
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• 239000012298 atmosphere Substances 0.000 description 6
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• FXRYMTMTGGFUJX-UHFFFAOYSA-N ethyl 10-(ethylamino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate Chemical compound C1CC2(NCC)CCC1CN(C1=O)C2=NC(C(=O)OCC)=C1OC(=O)C1=CC=CC=C1 FXRYMTMTGGFUJX-UHFFFAOYSA-N 0.000 description 1
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• LHYXLLAGXVGTOP-UHFFFAOYSA-N ethyl 10-amino-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate Chemical compound C1CC2(N)C3=NC(C(=O)OCC)=C(O)C(=O)N3CC1CC2 LHYXLLAGXVGTOP-UHFFFAOYSA-N 0.000 description 1
• BDLMFEHSOICKBL-UHFFFAOYSA-N ethyl 11-(((benzyloxy)carbonyl)(methyl)amino)-3-hydroxy-4-oxo-6,7,8,9,10,11-hexahydro-4h-7,10-methanopyrimido[1,2-a]azocine-2-carboxylate Chemical compound C1C2CCC1CN1C(=O)C(O)=C(C(=O)OCC)N=C1C2N(C)C(=O)OCC1=CC=CC=C1 BDLMFEHSOICKBL-UHFFFAOYSA-N 0.000 description 1
• PSADNECHGXKQOE-UHFFFAOYSA-N ethyl 11-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-7,8,10,11-tetrahydro-4 h,6h-8,11-methanopyrimido[2,1-d][1,5]oxazocine-2-carboxylate Chemical compound O=C1C(O)=C(C(=O)OCC)N=C2N1CCC(OC1)CC21NC(=O)OCC1=CC=CC=C1 PSADNECHGXKQOE-UHFFFAOYSA-N 0.000 description 1
• NMUSYXKJKMCCQQ-UHFFFAOYSA-N ethyl 2-[2-fluoroethyl(methyl)amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)N(C)CCF NMUSYXKJKMCCQQ-UHFFFAOYSA-N 0.000 description 1
• JYWNRMLNNCPYNG-UHFFFAOYSA-N ethyl 2-[3-(chloromethyl)-1-(phenylmethoxycarbonylamino)cyclohexyl]-5-hydroxy-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound N1C(=O)C(O)=C(C(=O)OCC)N=C1C1(NC(=O)OCC=2C=CC=CC=2)CC(CCl)CCC1 JYWNRMLNNCPYNG-UHFFFAOYSA-N 0.000 description 1
• ODMUVMKOFCNYPA-UHFFFAOYSA-N ethyl 2-[4-(hydroxymethyl)piperidin-1-yl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound CCOC(=O)C=1N=C(N2CCC(CO)CC2)NC(=O)C=1OCC1=CC=CC=C1 ODMUVMKOFCNYPA-UHFFFAOYSA-N 0.000 description 1
• TWHIEBALUKJYQQ-UHFFFAOYSA-N ethyl 2-[4-(hydroxymethyl)piperidin-1-yl]-5-phenylmethoxy-6-prop-2-enoxypyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC(N2CCC(CO)CC2)=NC(OCC=C)=C1OCC1=CC=CC=C1 TWHIEBALUKJYQQ-UHFFFAOYSA-N 0.000 description 1
• IBZUBTZCMSAIJM-UHFFFAOYSA-N ethyl 2-methylsulfanyl-5-phenylmethoxy-6-prop-2-enoxypyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC(SC)=NC(OCC=C)=C1OCC1=CC=CC=C1 IBZUBTZCMSAIJM-UHFFFAOYSA-N 0.000 description 1
• TZKNKEVYMAACRD-UHFFFAOYSA-N ethyl 2-methylsulfonyl-5-phenylmethoxy-6-prop-2-enoxypyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC(S(C)(=O)=O)=NC(OCC=C)=C1OCC1=CC=CC=C1 TZKNKEVYMAACRD-UHFFFAOYSA-N 0.000 description 1
• PHSWWKXTGAJPCQ-UHFFFAOYSA-N ethyl 2-phenylmethoxyacetate Chemical compound CCOC(=O)COCC1=CC=CC=C1 PHSWWKXTGAJPCQ-UHFFFAOYSA-N 0.000 description 1
• RNYCKGSYBGEKLF-UHFFFAOYSA-N ethyl 3-(benzoyloxy)-11-(((benzyloxy)carbonyl)(methyl)amino)-4-oxo-6,7,8,9,10,11-hexahydro-4h-7,10-methanopyrimido[1,2-a]azocine-2-carboxylate Chemical compound CCOC(=O)C=1N=C2C(N(C)C(=O)OCC=3C=CC=CC=3)C(C3)CCC3CN2C(=O)C=1OC(=O)C1=CC=CC=C1 RNYCKGSYBGEKLF-UHFFFAOYSA-N 0.000 description 1
• HAUPZPCWLBZNFV-UHFFFAOYSA-N ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4h-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate Chemical compound CCOC(=O)C=1N=C2N(CC3)CCC3CN2C(=O)C=1OCC1=CC=CC=C1 HAUPZPCWLBZNFV-UHFFFAOYSA-N 0.000 description 1
• YFUPZAKVUIHHQG-UHFFFAOYSA-N ethyl 5-benzoyloxy-2-[1-(2-benzoyloxyethoxy)-4-(hydroxymethyl)cyclohexyl]-4-oxo-1h-pyrimidine-6-carboxylate Chemical compound CCOC(=O)C=1N=C(C2(CCC(CO)CC2)OCCOC(=O)C=2C=CC=CC=2)NC(=O)C=1OC(=O)C1=CC=CC=C1 YFUPZAKVUIHHQG-UHFFFAOYSA-N 0.000 description 1
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