TWI378933B - Morpholinopurine derivatives - Google Patents

Info

Publication number

TWI378933B

TWI378933B TW098134442A TW98134442A TWI378933B TW I378933 B TWI378933 B TW I378933B TW 098134442 A TW098134442 A TW 098134442A TW 98134442 A TW98134442 A TW 98134442A TW I378933 B TWI378933 B TW I378933B

Authority

TW

Taiwan

Prior art keywords

group

mmol

compound

substituents selected

amine

Prior art date

2008-10-14

Links

• Espacenet
• Global Dossier
• Discuss

• IBVOXEAVUMUIBU-UHFFFAOYSA-N 4-(7h-purin-2-yl)morpholine Chemical class C1COCCN1C1=NC=C(NC=N2)C2=N1 IBVOXEAVUMUIBU-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 284
• 125000001424 substituent group Chemical group 0.000 claims description 263
• 125000000217 alkyl group Chemical group 0.000 claims description 120
• -1 diylamino group Chemical group 0.000 claims description 89
• 125000003282 alkyl amino group Chemical group 0.000 claims description 65
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 57
• 206010028980 Neoplasm Diseases 0.000 claims description 42
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 27
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 27
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000000468 ketone group Chemical group 0.000 claims description 15
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 14
• 239000002246 antineoplastic agent Substances 0.000 claims description 14
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 13
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
• 238000006467 substitution reaction Methods 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 229960005181 morphine Drugs 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 8
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 8
• 229940124597 therapeutic agent Drugs 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 7
• 229960002930 sirolimus Drugs 0.000 claims description 7
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
• 108091007960 PI3Ks Proteins 0.000 claims description 6
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims description 6
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 6
• 108091000080 Phosphotransferase Proteins 0.000 claims description 6
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 102000020233 phosphotransferase Human genes 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
• 206010017758 gastric cancer Diseases 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 150000003904 phospholipids Chemical class 0.000 claims description 5
• 201000011549 stomach cancer Diseases 0.000 claims description 5
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
• 108030003815 Inositol 3-kinases Proteins 0.000 claims description 4
• 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims description 4
• 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims description 4
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 4
• 125000002723 alicyclic group Chemical group 0.000 claims description 4
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 4
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 206010046766 uterine cancer Diseases 0.000 claims description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 239000003112 inhibitor Substances 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims description 2
• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 2
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 1
• 125000001188 haloalkyl group Chemical group 0.000 claims 1
• 229910021653 sulphate ion Inorganic materials 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 710
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 425
• 235000019439 ethyl acetate Nutrition 0.000 description 327
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 306
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 241
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 159
• 239000011541 reaction mixture Substances 0.000 description 153
• 238000005160 1H NMR spectroscopy Methods 0.000 description 152
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 131
• 239000000243 solution Substances 0.000 description 124
• 101150041968 CDC13 gene Proteins 0.000 description 121
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
• 230000002829 reductive effect Effects 0.000 description 111
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 102
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 101
• 239000002904 solvent Substances 0.000 description 99
• 239000000203 mixture Substances 0.000 description 95
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 88
• 238000003756 stirring Methods 0.000 description 80
• 229940086542 triethylamine Drugs 0.000 description 80
• 239000012044 organic layer Substances 0.000 description 79
• 239000007787 solid Substances 0.000 description 73
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 71
• 238000006243 chemical reaction Methods 0.000 description 66
• 239000013078 crystal Substances 0.000 description 62
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 59
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 53
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 53
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 52
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 50
• 238000001914 filtration Methods 0.000 description 50
• 238000001816 cooling Methods 0.000 description 46
• 229920006395 saturated elastomer Polymers 0.000 description 46
• 238000000034 method Methods 0.000 description 45
• 239000000706 filtrate Substances 0.000 description 38
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 38
• 235000019341 magnesium sulphate Nutrition 0.000 description 38
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• 235000017557 sodium bicarbonate Nutrition 0.000 description 35
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 35
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 34
• 239000002585 base Substances 0.000 description 33
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 32
• 150000001412 amines Chemical class 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 29
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000000725 suspension Substances 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• 238000003786 synthesis reaction Methods 0.000 description 25
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 24
• 230000015572 biosynthetic process Effects 0.000 description 24
• 235000019441 ethanol Nutrition 0.000 description 23
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 23
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 229910052739 hydrogen Inorganic materials 0.000 description 21
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 235000011054 acetic acid Nutrition 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 125000006239 protecting group Chemical group 0.000 description 18
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 201000011510 cancer Diseases 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 15
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 13
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 13
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 13
• 230000000694 effects Effects 0.000 description 12
• 230000002401 inhibitory effect Effects 0.000 description 12
• 230000000259 anti-tumor effect Effects 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 10
• 230000035484 reaction time Effects 0.000 description 10
• 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 10
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 150000003973 alkyl amines Chemical class 0.000 description 9
• OXKUGIFNIUUKAW-UHFFFAOYSA-N n,n-dimethylformamide;hydrazine Chemical compound NN.CN(C)C=O OXKUGIFNIUUKAW-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 239000000654 additive Substances 0.000 description 8
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 239000011777 magnesium Substances 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 7
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
• 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 7
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 7
• 230000007730 Akt signaling Effects 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 230000000996 additive effect Effects 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
• 235000019253 formic acid Nutrition 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
• 239000011259 mixed solution Substances 0.000 description 7
• 239000012046 mixed solvent Substances 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
• 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 6
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 230000004913 activation Effects 0.000 description 6
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