JP5595727B2 - Ｃ−ｋｉｔキナーゼ阻害法 - Google Patents

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Publication number

JP5595727B2

JP5595727B2 JP2009506778A JP2009506778A JP5595727B2 JP 5595727 B2 JP5595727 B2 JP 5595727B2 JP 2009506778 A JP2009506778 A JP 2009506778A JP 2009506778 A JP2009506778 A JP 2009506778A JP 5595727 B2 JP5595727 B2 JP 5595727B2

Authority

JP

Japan

Prior art keywords

mmol

carboxylic acid

phenyl

cyano

cyclohex

Prior art date

2006-04-20

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

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• 238000000034 method Methods 0.000 title claims description 91
• 108091000080 Phosphotransferase Proteins 0.000 title description 16
• 102000020233 phosphotransferase Human genes 0.000 title description 16
• 230000005764 inhibitory process Effects 0.000 title description 10
• 150000001875 compounds Chemical class 0.000 claims description 314
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 18
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 150000004677 hydrates Chemical class 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 8
• 238000001959 radiotherapy Methods 0.000 claims description 8
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 7
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 6
• 208000008585 mastocytosis Diseases 0.000 claims description 3
• 210000003630 histaminocyte Anatomy 0.000 claims description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 288
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 190
• -1 2,2,4-trimethylpentyl Chemical group 0.000 description 140
• 239000000203 mixture Substances 0.000 description 140
• 239000000243 solution Substances 0.000 description 111
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 103
• 238000001819 mass spectrum Methods 0.000 description 100
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• 235000019439 ethyl acetate Nutrition 0.000 description 92
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
• 238000005160 1H NMR spectroscopy Methods 0.000 description 85
• 239000007787 solid Substances 0.000 description 85
• 238000006243 chemical reaction Methods 0.000 description 79
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 78
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 77
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
• 239000011734 sodium Substances 0.000 description 65
• 229910052739 hydrogen Inorganic materials 0.000 description 49
• 239000001257 hydrogen Substances 0.000 description 47
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
• XTDRPNJABDWQFI-UHFFFAOYSA-N 5-cyano-1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC(C#N)=CN1 XTDRPNJABDWQFI-UHFFFAOYSA-N 0.000 description 43
• 125000003277 amino group Chemical group 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• 238000011282 treatment Methods 0.000 description 41
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 239000002904 solvent Substances 0.000 description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 210000004027 cell Anatomy 0.000 description 36
• 239000000741 silica gel Substances 0.000 description 34
• 229910002027 silica gel Inorganic materials 0.000 description 34
• 208000035475 disorder Diseases 0.000 description 33
• 239000012044 organic layer Substances 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• 229910052757 nitrogen Inorganic materials 0.000 description 31
• 239000000377 silicon dioxide Substances 0.000 description 31
• 125000000217 alkyl group Chemical group 0.000 description 29
• 229920006395 saturated elastomer Polymers 0.000 description 29
• 125000003118 aryl group Chemical group 0.000 description 27
• 150000002431 hydrogen Chemical class 0.000 description 27
• 206010028980 Neoplasm Diseases 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• 230000002829 reductive effect Effects 0.000 description 26
• 229910052760 oxygen Inorganic materials 0.000 description 24
• 238000003818 flash chromatography Methods 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 20
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• 125000003545 alkoxy group Chemical group 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• 125000004076 pyridyl group Chemical group 0.000 description 18
• 239000011780 sodium chloride Substances 0.000 description 18
• AYFFPEOVSJSGAT-UHFFFAOYSA-N 5-cyano-n-[2-(cyclohexen-1-yl)-4-piperidin-4-ylphenyl]-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C(C#N)=CNC=1C(=O)NC1=CC=C(C2CCNCC2)C=C1C1=CCCCC1 AYFFPEOVSJSGAT-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• 238000004007 reversed phase HPLC Methods 0.000 description 16
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000006069 Suzuki reaction reaction Methods 0.000 description 15
• 125000003282 alkyl amino group Chemical group 0.000 description 15
• 125000004122 cyclic group Chemical group 0.000 description 15
• 125000000753 cycloalkyl group Chemical group 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 235000019198 oils Nutrition 0.000 description 15
• 125000001424 substituent group Chemical group 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 14
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• 125000004093 cyano group Chemical group *C#N 0.000 description 14
• 125000002541 furyl group Chemical group 0.000 description 14
• 125000005842 heteroatom Chemical group 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 238000006467 substitution reaction Methods 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
• 125000001309 chloro group Chemical group Cl* 0.000 description 13
• 125000002883 imidazolyl group Chemical group 0.000 description 13
• 239000001301 oxygen Substances 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 12
• 229910052736 halogen Inorganic materials 0.000 description 12
• 150000002367 halogens Chemical group 0.000 description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• 239000003826 tablet Substances 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• 125000001072 heteroaryl group Chemical group 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• 150000001204 N-oxides Chemical class 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 10
• 125000000168 pyrrolyl group Chemical group 0.000 description 10
• 125000005942 tetrahydropyridyl group Chemical group 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 125000003710 aryl alkyl group Chemical group 0.000 description 9
• 125000004663 dialkyl amino group Chemical group 0.000 description 9
• 125000000842 isoxazolyl group Chemical group 0.000 description 9
• 229910052751 metal Inorganic materials 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• 125000002971 oxazolyl group Chemical group 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 238000012552 review Methods 0.000 description 9
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
• HHHCADSYQQJUGV-UHFFFAOYSA-N 5-cyanofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)O1 HHHCADSYQQJUGV-UHFFFAOYSA-N 0.000 description 8
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• 125000004103 aminoalkyl group Chemical group 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• 125000001188 haloalkyl group Chemical group 0.000 description 8
• 125000004475 heteroaralkyl group Chemical group 0.000 description 8
• 125000005191 hydroxyalkylamino group Chemical group 0.000 description 8
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical group ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
• BNQGKHUEVQWESM-UHFFFAOYSA-M potassium;4-cyano-1-(2-trimethylsilylethoxymethyl)imidazole-2-carboxylate Chemical compound [K+].C[Si](C)(C)CCOCN1C=C(C#N)N=C1C([O-])=O BNQGKHUEVQWESM-UHFFFAOYSA-M 0.000 description 8
• 238000012746 preparative thin layer chromatography Methods 0.000 description 8
• 238000010898 silica gel chromatography Methods 0.000 description 8
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 7
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 7
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• XZWQKJXJNKYMAP-UHFFFAOYSA-N cyclohexen-1-ylboronic acid Chemical compound OB(O)C1=CCCCC1 XZWQKJXJNKYMAP-UHFFFAOYSA-N 0.000 description 7
• 125000004990 dihydroxyalkyl group Chemical group 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 238000002875 fluorescence polarization Methods 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 230000002062 proliferating effect Effects 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• 239000002002 slurry Substances 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 238000002560 therapeutic procedure Methods 0.000 description 7
• PAMSSXMKTNVDCR-UHFFFAOYSA-N 1-(3-bromo-4-nitrophenyl)-4-methylpiperazine Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(Br)=C1 PAMSSXMKTNVDCR-UHFFFAOYSA-N 0.000 description 6
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• SQMINWFWFXVWHK-UHFFFAOYSA-N 4-cyano-1-(2-trimethylsilylethoxymethyl)imidazole-2-carboxylic acid Chemical compound C[Si](C)(C)CCOCN1C=C(C#N)N=C1C(O)=O SQMINWFWFXVWHK-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
• 239000004480 active ingredient Substances 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 239000011230 binding agent Substances 0.000 description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
• 229940002612 prodrug Drugs 0.000 description 6
• 239000000651 prodrug Substances 0.000 description 6
• 230000035755 proliferation Effects 0.000 description 6
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 125000001544 thienyl group Chemical group 0.000 description 6
• 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 6
• DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• FIVQWANVHJBLAY-UHFFFAOYSA-N 1-(2-trimethylsilylethoxymethyl)imidazole-4-carbonitrile Chemical compound C[Si](C)(C)CCOCN1C=NC(C#N)=C1 FIVQWANVHJBLAY-UHFFFAOYSA-N 0.000 description 5
• BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 125000001246 bromo group Chemical group Br* 0.000 description 5
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• 208000035269 cancer or benign tumor Diseases 0.000 description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
• BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
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• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 5
• 238000012377 drug delivery Methods 0.000 description 5
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
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• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000000523 sample Substances 0.000 description 5
• 238000010561 standard procedure Methods 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• NXZKMPZVGNXFAM-UHFFFAOYSA-N tert-butyl 4-[4-amino-3-(cyclohexen-1-yl)phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(N)C(C=2CCCCC=2)=C1 NXZKMPZVGNXFAM-UHFFFAOYSA-N 0.000 description 5
• 210000004881 tumor cell Anatomy 0.000 description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• SWPGDCRPXQMSIA-UHFFFAOYSA-N 4-[4-[(5-cyano-1h-imidazole-2-carbonyl)amino]-3-(cyclohexen-1-yl)phenyl]-n-(2-hydroxyethyl)piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCO)CCC1C(C=C1C=2CCCCC=2)=CC=C1NC(=O)C1=NC(C#N)=CN1 SWPGDCRPXQMSIA-UHFFFAOYSA-N 0.000 description 4
• XPCQXAQALLRVJQ-UHFFFAOYSA-N 5-cyano-n-[2-(cyclohexen-1-yl)-4-piperidin-4-ylphenyl]-1h-imidazole-2-carboxamide Chemical compound N=1C=C(C#N)NC=1C(=O)NC1=CC=C(C2CCNCC2)C=C1C1=CCCCC1 XPCQXAQALLRVJQ-UHFFFAOYSA-N 0.000 description 4
• VLZZMVPPSQPHMQ-UHFFFAOYSA-N 5-cyanofuran-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)O1 VLZZMVPPSQPHMQ-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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