PT1183256E - Derivados de purina, processo de preparação e composições farmacêuticas que os contêm - Google Patents

Info

Publication number

PT1183256E

PT1183256E PT00929625T PT00929625T PT1183256E PT 1183256 E PT1183256 E PT 1183256E PT 00929625 T PT00929625 T PT 00929625T PT 00929625 T PT00929625 T PT 00929625T PT 1183256 E PT1183256 E PT 1183256E

Authority

PT

Portugal

Prior art keywords

amino

cyclopentyl

formula

trans

aminocyclohexyl

Prior art date

1999-05-21

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
• 238000002360 preparation method Methods 0.000 title claims description 7
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 5
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
• -1 phenyl radicals Chemical class 0.000 claims description 292
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 243
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 101
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 68
• 238000000034 method Methods 0.000 claims description 61
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
• 150000003254 radicals Chemical class 0.000 claims description 54
• 125000004432 carbon atom Chemical group C* 0.000 claims description 50
• 238000006243 chemical reaction Methods 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 22
• 239000011707 mineral Substances 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy 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 16
• 125000006239 protecting group Chemical group 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 150000007522 mineralic acids Chemical class 0.000 claims description 10
• 150000007524 organic acids Chemical class 0.000 claims description 10
• 150000007530 organic bases Chemical class 0.000 claims description 9
• ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 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 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 235000005985 organic acids Nutrition 0.000 claims description 7
• 238000007254 oxidation reaction Methods 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003158 alcohol group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 5
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• 241000233866 Fungi Species 0.000 claims description 5
• 150000001299 aldehydes Chemical class 0.000 claims description 5
• 230000002927 anti-mitotic effect Effects 0.000 claims description 5
• 238000002512 chemotherapy Methods 0.000 claims description 5
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 150000002148 esters Chemical group 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 238000006722 reduction reaction Methods 0.000 claims description 5
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 150000002576 ketones Chemical group 0.000 claims description 4
• 150000003462 sulfoxides Chemical class 0.000 claims description 4
• PNDPNCSMYVPNAC-UFLMWKHXSA-N Cl.Cl.C1C[C@@H](N)CC[C@@H]1NC1=NC(NC=2C=CC(CC#N)=CC=2)=C(N=CN2C3CCCC3)C2=N1 Chemical compound Cl.Cl.C1C[C@@H](N)CC[C@@H]1NC1=NC(NC=2C=CC(CC#N)=CC=2)=C(N=CN2C3CCCC3)C2=N1 PNDPNCSMYVPNAC-UFLMWKHXSA-N 0.000 claims description 3
• XXJUWWSURYTSCT-HEOZJBRKSA-N Cl.Cl.COc1ccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 Chemical compound Cl.Cl.COc1ccc(Nc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 XXJUWWSURYTSCT-HEOZJBRKSA-N 0.000 claims description 3
• 230000002555 anti-neurodegenerative effect Effects 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 230000009223 neuronal apoptosis Effects 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 238000007127 saponification reaction Methods 0.000 claims description 3
• 125000004001 thioalkyl group Chemical group 0.000 claims description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• ZPFSQNUOEIAPRQ-PVPJKCDMSA-N Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(cc2)N2CCOCC2)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(cc2)N2CCOCC2)c2ncn(C3CCCC3)c2n1 ZPFSQNUOEIAPRQ-PVPJKCDMSA-N 0.000 claims description 2
• 230000006909 anti-apoptosis Effects 0.000 claims description 2
• 239000003638 chemical reducing agent Substances 0.000 claims description 2
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
• 230000001537 neural effect Effects 0.000 claims description 2
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
• BIULRBPHIVGVNR-WKILWMFISA-N N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cc(cc(c2)C(O)=O)C(O)=O)c2ncn(C3CCCC3)c2n1 Chemical compound N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cc(cc(c2)C(O)=O)C(O)=O)c2ncn(C3CCCC3)c2n1 BIULRBPHIVGVNR-WKILWMFISA-N 0.000 claims 1
• RGKCQSDVAHPJRB-SAABIXHNSA-N N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(cc2)C#N)c2ncn(C3CCCC3)c2n1 Chemical compound N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(cc2)C#N)c2ncn(C3CCCC3)c2n1 RGKCQSDVAHPJRB-SAABIXHNSA-N 0.000 claims 1
• 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
• 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
• 201000010099 disease Diseases 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
• 238000003379 elimination reaction Methods 0.000 claims 1
• 150000002828 nitro derivatives Chemical class 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• 229910052760 oxygen Inorganic materials 0.000 claims 1
• 239000001301 oxygen Substances 0.000 claims 1
• 239000000047 product Substances 0.000 description 545
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 390
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 370
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 302
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 276
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 260
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 185
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 172
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 152
• 239000000377 silicon dioxide Substances 0.000 description 130
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 117
• 239000003480 eluent Substances 0.000 description 112
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 110
• 238000005481 NMR spectroscopy Methods 0.000 description 110
• VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 91
• 235000019439 ethyl acetate Nutrition 0.000 description 90
• 239000013078 crystal Substances 0.000 description 87
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
• 229910021529 ammonia Inorganic materials 0.000 description 78
• 239000002904 solvent Substances 0.000 description 76
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 74
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 65
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 62
• 239000000243 solution Substances 0.000 description 61
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
• 238000000746 purification Methods 0.000 description 57
• 230000002829 reductive effect Effects 0.000 description 52
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
• 238000004587 chromatography analysis Methods 0.000 description 39
• 238000003756 stirring Methods 0.000 description 35
• 239000000203 mixture Substances 0.000 description 30
• 229920006395 saturated elastomer Polymers 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 239000011780 sodium chloride Substances 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 24
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 20
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
• 239000007864 aqueous solution Substances 0.000 description 17
• BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 16
• 235000010755 mineral Nutrition 0.000 description 15
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 14
• 229910000024 caesium carbonate Inorganic materials 0.000 description 14
• 230000009471 action Effects 0.000 description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 11
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• GIZCKBSSWNIUMZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(CN)C=C1 GIZCKBSSWNIUMZ-UHFFFAOYSA-N 0.000 description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• 150000007513 acids Chemical class 0.000 description 8
• 238000009938 salting Methods 0.000 description 8
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 238000010561 standard procedure Methods 0.000 description 6
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• 108091000080 Phosphotransferase Proteins 0.000 description 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 102000020233 phosphotransferase Human genes 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 4
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
• XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 230000022131 cell cycle Effects 0.000 description 4
• 238000006482 condensation reaction Methods 0.000 description 4
• 239000006071 cream Substances 0.000 description 4
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
• 238000002329 infrared spectrum Methods 0.000 description 4
• 230000000873 masking effect Effects 0.000 description 4
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 235000011181 potassium carbonates Nutrition 0.000 description 4
• 150000003212 purines Chemical class 0.000 description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• XDPCNPCKDGQBAN-UHFFFAOYSA-N 3-hydroxytetrahydrofuran Chemical compound OC1CCOC1 XDPCNPCKDGQBAN-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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