TW201217362A

TW201217362A - Heteroaryls and uses thereof

Heteroaryls and uses thereof Download PDF

Info

Publication number: TW201217362A
Authority: TW; Taiwan
Prior art keywords: group; compound; sulfur; nitrogen; oxygen
Prior art date: 2010-08-11

Application number

TW100128763A

Other languages

English (en)

Chinese (zh)

Inventor

Tricia J Vos

Courtney A Cullis

Krista E Granger

Jianping Guo

Masaaki Hirose

Gang Li

Miho Mizutani

Original Assignee

Millennium Pharm Inc

Priority date

2010-08-11

Filing date

2011-08-11

Publication date

2012-05-01

2011-08-11 Application filed by Millennium Pharm Inc filed Critical Millennium Pharm Inc

2012-05-01 Publication of TW201217362A publication Critical patent/TW201217362A/zh

Links

125000001072 heteroaryl group Chemical group 0.000 title claims description 69
150000001875 compounds Chemical class 0.000 claims abstract description 209
101000605630 Homo sapiens Phosphatidylinositol 3-kinase catalytic subunit type 3 Proteins 0.000 claims abstract description 28
102100038329 Phosphatidylinositol 3-kinase catalytic subunit type 3 Human genes 0.000 claims abstract description 28
230000002757 inflammatory effect Effects 0.000 claims abstract description 11
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
230000002062 proliferating effect Effects 0.000 claims abstract description 10
108091007960 PI3Ks Proteins 0.000 claims abstract description 4
102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims abstract 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 171
239000000203 mixture Substances 0.000 claims description 133
229910052757 nitrogen Inorganic materials 0.000 claims description 110
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 95
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 94
229910052760 oxygen Inorganic materials 0.000 claims description 94
239000001301 oxygen Substances 0.000 claims description 94
-1 ethoxymethylene Chemical group 0.000 claims description 92
229910052717 sulfur Inorganic materials 0.000 claims description 85
239000011593 sulfur Substances 0.000 claims description 85
125000003118 aryl group Chemical group 0.000 claims description 84
125000001931 aliphatic group Chemical group 0.000 claims description 74
125000005842 heteroatom Chemical group 0.000 claims description 73
125000000623 heterocyclic group Chemical group 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 55
125000000217 alkyl group Chemical group 0.000 claims description 52
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
125000004429 atom Chemical group 0.000 claims description 20
239000007789 gas Substances 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
125000002950 monocyclic group Chemical group 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
206010020751 Hypersensitivity Diseases 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000002923 oximes Chemical class 0.000 claims description 5
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 4
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
206010014733 Endometrial cancer Diseases 0.000 claims description 4
206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
235000010233 benzoic acid Nutrition 0.000 claims description 4
239000004305 biphenyl Substances 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000002526 effect on cardiovascular system Effects 0.000 claims description 4
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 3
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
206010005003 Bladder cancer Diseases 0.000 claims description 3
208000003174 Brain Neoplasms Diseases 0.000 claims description 3
206010006187 Breast cancer Diseases 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
208000006029 Cardiomegaly Diseases 0.000 claims description 3
206010009944 Colon cancer Diseases 0.000 claims description 3
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
208000032612 Glial tumor Diseases 0.000 claims description 3
206010018338 Glioma Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
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206010060862 Prostate cancer Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
206010038389 Renal cancer Diseases 0.000 claims description 3
208000007536 Thrombosis Diseases 0.000 claims description 3
208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
208000038016 acute inflammation Diseases 0.000 claims description 3
230000006022 acute inflammation Effects 0.000 claims description 3
230000000172 allergic effect Effects 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
208000037976 chronic inflammation Diseases 0.000 claims description 3
230000006020 chronic inflammation Effects 0.000 claims description 3
208000029742 colonic neoplasm Diseases 0.000 claims description 3
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125000004494 ethyl ester group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
208000005017 glioblastoma Diseases 0.000 claims description 3
231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 3
201000010982 kidney cancer Diseases 0.000 claims description 3
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208000020816 lung neoplasm Diseases 0.000 claims description 3
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
201000001441 melanoma Diseases 0.000 claims description 3
201000002528 pancreatic cancer Diseases 0.000 claims description 3
208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
239000002689 soil Substances 0.000 claims description 3
125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
201000002510 thyroid cancer Diseases 0.000 claims description 3
201000005112 urinary bladder cancer Diseases 0.000 claims description 3
VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 claims description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical compound NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 claims description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
241000237536 Mytilus edulis Species 0.000 claims description 2
206010033128 Ovarian cancer Diseases 0.000 claims description 2
206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
206010017758 gastric cancer Diseases 0.000 claims description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
235000020638 mussel Nutrition 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 2
210000002784 stomach Anatomy 0.000 claims description 2
201000011549 stomach cancer Diseases 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims 1
229910002651 NO3 Inorganic materials 0.000 claims 1
125000005418 aryl aryl group Chemical group 0.000 claims 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
239000004519 grease Substances 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
125000006327 phenyl hydrazinyl group Chemical group [H]N(*)N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims 1
238000004513 sizing Methods 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 10
208000027866 inflammatory disease Diseases 0.000 abstract description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 124
239000000243 solution Substances 0.000 description 101
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 100
239000011541 reaction mixture Substances 0.000 description 85
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 78
235000019439 ethyl acetate Nutrition 0.000 description 61
238000000034 method Methods 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
238000004440 column chromatography Methods 0.000 description 37
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
239000002585 base Substances 0.000 description 31
210000004027 cell Anatomy 0.000 description 31
206010028980 Neoplasm Diseases 0.000 description 29
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
201000011510 cancer Diseases 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000002609 medium Substances 0.000 description 18
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 15
238000000746 purification Methods 0.000 description 15
239000011734 sodium Substances 0.000 description 15
238000007876 drug discovery Methods 0.000 description 14
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
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 11
108091008611 Protein Kinase B Proteins 0.000 description 11
102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 11
239000012267 brine Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
125000001041 indolyl group Chemical group 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000007858 starting material Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
239000007864 aqueous solution Substances 0.000 description 10
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ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 10
235000018102 proteins Nutrition 0.000 description 10
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
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125000004432 carbon atom Chemical group C* 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
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OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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125000002619 bicyclic group Chemical group 0.000 description 6
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
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229910052740 iodine Inorganic materials 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
229920001223 polyethylene glycol Polymers 0.000 description 6
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