JP5675360B2 - Ｐｉ３ｋ阻害剤としてのチエノピリミジエン誘導体 - Google Patents

Info

Publication number

JP5675360B2

JP5675360B2 JP2010530548A JP2010530548A JP5675360B2 JP 5675360 B2 JP5675360 B2 JP 5675360B2 JP 2010530548 A JP2010530548 A JP 2010530548A JP 2010530548 A JP2010530548 A JP 2010530548A JP 5675360 B2 JP5675360 B2 JP 5675360B2

Authority

JP

Japan

Prior art keywords

thieno

morpholin

ylmethyl

indol

diaza

Prior art date

2007-10-26

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

Links

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• 239000012828 PI3K inhibitor Substances 0.000 title 1
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 255
• -1 2,7-diaza-spiro [3.5] non-2-ylmethyl Chemical group 0.000 claims description 162
• 229920006395 saturated elastomer Polymers 0.000 claims description 46
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 17
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000001041 indolyl group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229910052796 boron Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• CJHGBUFGBANITH-UHFFFAOYSA-N 1-[2-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1CN(C(=O)C)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 CJHGBUFGBANITH-UHFFFAOYSA-N 0.000 claims description 2
• RKKKKOZHFZWVCC-UHFFFAOYSA-N 2-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2,7-diazaspiro[3.5]nonane-7-carboxamide Chemical compound C1CN(C(=O)N)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 RKKKKOZHFZWVCC-UHFFFAOYSA-N 0.000 claims description 2
• YTKVTIGWSOFONQ-UHFFFAOYSA-N 2-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethyl-2,7-diazaspiro[3.5]nonane-7-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 YTKVTIGWSOFONQ-UHFFFAOYSA-N 0.000 claims description 2
• YSESYAULARMLRW-UHFFFAOYSA-N 4-[2-(5-fluoro-1h-indol-4-yl)-6-[(7-methylsulfonyl-2,7-diazaspiro[3.5]nonan-2-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 YSESYAULARMLRW-UHFFFAOYSA-N 0.000 claims description 2
• MFLJGTDDTWCCRW-UHFFFAOYSA-N 4-[6-(2,7-diazaspiro[3.5]nonan-2-ylmethyl)-2-(1h-indol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=4C=CNC=4C=CC=3)=NC(N3CCOCC3)=C2SC=1CN(C1)CC21CCNCC2 MFLJGTDDTWCCRW-UHFFFAOYSA-N 0.000 claims description 2
• VBROLTDPOWFKTL-UHFFFAOYSA-N 4-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1-oxa-4,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=C2NC=CC2=C1C(N=C1C=C(CN2CC3(CCNCC3)OCC2)SC1=1)=NC=1N1CCOCC1 VBROLTDPOWFKTL-UHFFFAOYSA-N 0.000 claims description 2
• XCYQDPCVXAVMPC-UHFFFAOYSA-N 7-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2,7-diazaspiro[3.5]nonan-3-one Chemical compound FC1=CC=C2NC=CC2=C1C(N=C1C=C(CN2CCC3(C(NC3)=O)CC2)SC1=1)=NC=1N1CCOCC1 XCYQDPCVXAVMPC-UHFFFAOYSA-N 0.000 claims description 2
• LISQRGKRBGUTAJ-UHFFFAOYSA-N 9-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1-oxa-4,9-diazaspiro[5.5]undecane Chemical compound FC1=CC=C2NC=CC2=C1C(N=C1C=C(CN2CCC3(CC2)OCCNC3)SC1=1)=NC=1N1CCOCC1 LISQRGKRBGUTAJ-UHFFFAOYSA-N 0.000 claims description 2
• YUEAEYBBCIZGSI-UHFFFAOYSA-N methyl 2-[[2-(5-fluoro-1h-indol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-2,7-diazaspiro[3.5]nonane-7-carboxylate Chemical compound C1CN(C(=O)OC)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 YUEAEYBBCIZGSI-UHFFFAOYSA-N 0.000 claims description 2
• IHQHYKUVUQXRGX-UHFFFAOYSA-N 4-[2-(5-fluoro-1h-indol-4-yl)-6-[(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCC11CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=CNC=3C=CC=2F)C1 IHQHYKUVUQXRGX-UHFFFAOYSA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 232
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 200
• 239000007787 solid Substances 0.000 description 191
• 238000000034 method Methods 0.000 description 148
• 239000000243 solution Substances 0.000 description 138
• 238000005481 NMR spectroscopy Methods 0.000 description 131
• 239000000203 mixture Substances 0.000 description 109
• 239000011541 reaction mixture Substances 0.000 description 93
• 238000006069 Suzuki reaction reaction Methods 0.000 description 89
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
• 230000002829 reductive effect Effects 0.000 description 63
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 50
• 238000002360 preparation method Methods 0.000 description 50
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 239000011734 sodium Substances 0.000 description 41
• 235000019439 ethyl acetate Nutrition 0.000 description 38
• 238000004440 column chromatography Methods 0.000 description 34
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 32
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• 238000010511 deprotection reaction Methods 0.000 description 29
• 239000000725 suspension Substances 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• 239000012267 brine Substances 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 23
• 239000012230 colorless oil Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 108091007960 PI3Ks Proteins 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 239000010410 layer Substances 0.000 description 19
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 17
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
• 239000006071 cream Substances 0.000 description 17
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 238000002953 preparative HPLC Methods 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 238000001914 filtration Methods 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 238000000039 preparative column chromatography Methods 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• QOIARYNCRPZCTG-UHFFFAOYSA-N 7-methyl-2,7-diazaspiro[3.5]nonane Chemical compound C1CN(C)CCC11CNC1 QOIARYNCRPZCTG-UHFFFAOYSA-N 0.000 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 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 9
• PFAKZIZFIXKDFP-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbaldehyde Chemical compound C=12SC(C=O)=CC2=NC(Cl)=NC=1N1CCOCC1 PFAKZIZFIXKDFP-UHFFFAOYSA-N 0.000 description 8
• 239000006260 foam Substances 0.000 description 8
• 238000007429 general method Methods 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
• 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 8
• DDGJOTNSVPHXNT-UHFFFAOYSA-N 4-[6-(bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CBr)=CC2=NC(Cl)=NC=1N1CCOCC1 DDGJOTNSVPHXNT-UHFFFAOYSA-N 0.000 description 7
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
• 102000001708 Protein Isoforms Human genes 0.000 description 7
• 108010029485 Protein Isoforms Proteins 0.000 description 7
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
• 125000002619 bicyclic group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000001072 heteroaryl group Chemical group 0.000 description 7
• 239000002480 mineral oil Substances 0.000 description 7
• 235000010446 mineral oil Nutrition 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 238000006268 reductive amination reaction Methods 0.000 description 7
• FTTATHOUSOIFOQ-ZETCQYMHSA-N (8as)-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCC[C@H]21 FTTATHOUSOIFOQ-ZETCQYMHSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 230000002209 hydrophobic effect Effects 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000003765 sweetening agent Substances 0.000 description 6
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 5
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
• 229920002261 Corn starch Polymers 0.000 description 5
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 239000004480 active ingredient Substances 0.000 description 5
• 239000007900 aqueous suspension Substances 0.000 description 5
• 239000007859 condensation product Substances 0.000 description 5
• 239000008120 corn starch Substances 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• 238000000605 extraction Methods 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 239000000796 flavoring agent Substances 0.000 description 5
• 235000003599 food sweetener Nutrition 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 239000002245 particle Substances 0.000 description 5
• 125000004585 polycyclic heterocycle group Chemical group 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• 238000000825 ultraviolet detection Methods 0.000 description 5
• 239000000080 wetting agent Substances 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• USASUEYARBQNBM-UHFFFAOYSA-N 1h-indol-2-ylboronic acid Chemical compound C1=CC=C2NC(B(O)O)=CC2=C1 USASUEYARBQNBM-UHFFFAOYSA-N 0.000 description 4
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