CN104736533B - Vegfr3抑制剂 - Google Patents

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Publication number

CN104736533B

CN104736533B CN201380052158.7A CN201380052158A CN104736533B CN 104736533 B CN104736533 B CN 104736533B CN 201380052158 A CN201380052158 A CN 201380052158A CN 104736533 B CN104736533 B CN 104736533B

Authority

CN

China

Prior art keywords

base

phenyl

ethyl

amino

pyrimidine

Prior art date

2012-08-17

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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• 239000003112 inhibitor Substances 0.000 title description 23
• 101150009958 FLT4 gene Proteins 0.000 title 1
• 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 341
• 239000000203 mixture Substances 0.000 claims abstract description 171
• 238000000034 method Methods 0.000 claims abstract description 70
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 48
• 239000003814 drug Substances 0.000 claims abstract description 42
• 201000011510 cancer Diseases 0.000 claims abstract description 38
• 230000001629 suppression Effects 0.000 claims abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 201000010099 disease Diseases 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 265
• -1 cyclopropylidene Chemical group 0.000 claims description 246
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 235
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 206
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 113
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 110
• 125000001424 substituent group Chemical group 0.000 claims description 83
• 125000001072 heteroaryl group Chemical group 0.000 claims description 69
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 64
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 62
• 150000003839 salts Chemical class 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 45
• 238000002360 preparation method Methods 0.000 claims description 41
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 37
• 150000001408 amides Chemical class 0.000 claims description 33
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 33
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 229910021529 ammonia Inorganic materials 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 238000002560 therapeutic procedure Methods 0.000 claims description 15
• HXTJGVQFEGUXCX-UHFFFAOYSA-N cyclopropane;formamide Chemical compound C1CC1.NC=O HXTJGVQFEGUXCX-UHFFFAOYSA-N 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 230000036541 health Effects 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 7
• SRXXQJWEBRHOLZ-UHFFFAOYSA-N n-[2-[2-(2-anilino-5-chloropyrimidin-4-yl)ethyl]phenyl]cyclopropanecarboxamide Chemical compound N1=C(CCC=2C(=CC=CC=2)NC(=O)C2CC2)C(Cl)=CN=C1NC1=CC=CC=C1 SRXXQJWEBRHOLZ-UHFFFAOYSA-N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims description 4
• 201000008275 breast carcinoma Diseases 0.000 claims description 4
• PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• 201000010536 head and neck cancer Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000004979 cyclopentylene group Chemical group 0.000 claims description 2
• 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 claims 3
• DHNQEVGPZRYWCG-UHFFFAOYSA-N CC(C1=CC=C(C=C1)NC2=NC=C(C(=N2)CCC3=CC=CC=C3NC(=O)C4CC4)C(F)(F)F)NC(=O)C Chemical compound CC(C1=CC=C(C=C1)NC2=NC=C(C(=N2)CCC3=CC=CC=C3NC(=O)C4CC4)C(F)(F)F)NC(=O)C DHNQEVGPZRYWCG-UHFFFAOYSA-N 0.000 claims 2
• IQMWIZCNMFUFID-UHFFFAOYSA-N O=C(C1CC1)NC1=C(CCC2=NC(NC3=CC=C(C(F)(F)F)N=C3)=NC=C2C(F)(F)F)C=CC=C1 Chemical compound O=C(C1CC1)NC1=C(CCC2=NC(NC3=CC=C(C(F)(F)F)N=C3)=NC=C2C(F)(F)F)C=CC=C1 IQMWIZCNMFUFID-UHFFFAOYSA-N 0.000 claims 2
• 238000006073 displacement reaction Methods 0.000 claims 2
• RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims 2
• 210000001365 lymphatic vessel Anatomy 0.000 abstract description 26
• 230000002062 proliferating effect Effects 0.000 abstract description 3
• 239000002585 base Substances 0.000 description 288
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 197
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 125
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
• 239000007787 solid Substances 0.000 description 90
• 239000000243 solution Substances 0.000 description 90
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
• 238000000746 purification Methods 0.000 description 77
• 238000003756 stirring Methods 0.000 description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
• 235000002639 sodium chloride Nutrition 0.000 description 67
• 239000000377 silicon dioxide Substances 0.000 description 65
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
• 238000005160 1H NMR spectroscopy Methods 0.000 description 54
• 229910052681 coesite Inorganic materials 0.000 description 54
• 229910052906 cristobalite Inorganic materials 0.000 description 54
• 229910052682 stishovite Inorganic materials 0.000 description 54
• 229910052905 tridymite Inorganic materials 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
• 230000015572 biosynthetic process Effects 0.000 description 53
• 238000003786 synthesis reaction Methods 0.000 description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
• 239000002904 solvent Substances 0.000 description 42
• 239000003208 petroleum Substances 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
• 239000000725 suspension Substances 0.000 description 38
• 229960001866 silicon dioxide Drugs 0.000 description 37
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 36
• 239000000651 prodrug Substances 0.000 description 35
• 229940002612 prodrug Drugs 0.000 description 35
• QUERMGFVJPRMJL-UHFFFAOYSA-N tert-butyl azetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC1 QUERMGFVJPRMJL-UHFFFAOYSA-N 0.000 description 35
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 34
• 238000004440 column chromatography Methods 0.000 description 33
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 32
• 239000000741 silica gel Substances 0.000 description 32
• 229910002027 silica gel Inorganic materials 0.000 description 32
• 239000012453 solvate Substances 0.000 description 32
• 238000010898 silica gel chromatography Methods 0.000 description 31
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
• 230000002829 reductive effect Effects 0.000 description 30
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 25
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• 239000011780 sodium chloride Substances 0.000 description 24
• 239000010410 layer Substances 0.000 description 23
• 239000003921 oil Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 22
• 239000001257 hydrogen Substances 0.000 description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 21
• 238000009210 therapy by ultrasound Methods 0.000 description 21
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
• 150000002148 esters Chemical class 0.000 description 19
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
• 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 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 235000019253 formic acid Nutrition 0.000 description 18
• 239000000376 reactant Substances 0.000 description 18
• 230000008878 coupling Effects 0.000 description 17
• 238000010168 coupling process Methods 0.000 description 17
• 238000005859 coupling reaction Methods 0.000 description 17
• 230000000694 effects Effects 0.000 description 17
• 150000002500 ions Chemical class 0.000 description 17
• 239000012299 nitrogen atmosphere Substances 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 239000008346 aqueous phase Substances 0.000 description 16
• 229910000024 caesium carbonate Inorganic materials 0.000 description 16
• 239000003795 chemical substances by application Substances 0.000 description 16
• 229910052740 iodine Inorganic materials 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 16
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 238000005406 washing Methods 0.000 description 15
• YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 239000000523 sample Substances 0.000 description 14
• 239000003643 water by type Substances 0.000 description 14
• 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 13
• 229940076134 benzene Drugs 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 239000012071 phase Substances 0.000 description 13
• 230000008569 process Effects 0.000 description 13
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
• 239000007864 aqueous solution Substances 0.000 description 12
• 239000012298 atmosphere Substances 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 12
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 12
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 11
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 11
• 239000012065 filter cake Substances 0.000 description 11
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 239000006071 cream Substances 0.000 description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
• 238000001914 filtration Methods 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 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
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 101000742596 Homo sapiens Vascular endothelial growth factor C Proteins 0.000 description 9
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 102100038232 Vascular endothelial growth factor C Human genes 0.000 description 9
• 229910052794 bromium Inorganic materials 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
• 238000001514 detection method Methods 0.000 description 9
• 239000004519 grease Substances 0.000 description 9
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
• MUWHLDOWBATGDG-UHFFFAOYSA-N 1-(2-ethynylphenyl)cyclopropane-1-carboxamide Chemical compound C=1C=CC=C(C#C)C=1C1(C(=O)N)CC1 MUWHLDOWBATGDG-UHFFFAOYSA-N 0.000 description 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• 241000238370 Sepia Species 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000001556 precipitation Methods 0.000 description 8
• 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 8
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
• 101000742599 Homo sapiens Vascular endothelial growth factor D Proteins 0.000 description 7
• 102100038234 Vascular endothelial growth factor D Human genes 0.000 description 7
• 239000000443 aerosol Substances 0.000 description 7
• 150000001450 anions Chemical class 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 210000004369 blood Anatomy 0.000 description 7
• 239000008280 blood Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 239000011630 iodine Substances 0.000 description 7
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 7
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 7
• 239000008194 pharmaceutical composition Substances 0.000 description 7
• 210000003491 skin Anatomy 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• XCLKFXTWLPMSFY-UHFFFAOYSA-N tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1C1=CC=C(N)C=C1 XCLKFXTWLPMSFY-UHFFFAOYSA-N 0.000 description 7
• 230000001225 therapeutic effect Effects 0.000 description 7
• 238000012546 transfer Methods 0.000 description 7
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