JP2009007348A5 - - Google Patents
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- Publication number
- JP2009007348A5 JP2009007348A5 JP2008142698A JP2008142698A JP2009007348A5 JP 2009007348 A5 JP2009007348 A5 JP 2009007348A5 JP 2008142698 A JP2008142698 A JP 2008142698A JP 2008142698 A JP2008142698 A JP 2008142698A JP 2009007348 A5 JP2009007348 A5 JP 2009007348A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- imaging agent
- agent according
- ring
- phenyl
- Prior art date
- 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.)
- Granted
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 imidazo pyrimidyl group Chemical group 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012216 imaging agent Substances 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 230000002285 radioactive effect Effects 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- QTXWFLGYBJJQCK-UHFFFAOYSA-N 1-[4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 QTXWFLGYBJJQCK-UHFFFAOYSA-N 0.000 description 4
- YUPOSLKWJRFUAQ-UHFFFAOYSA-N 2-bromo-1-[4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 YUPOSLKWJRFUAQ-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 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 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MJRBEDUTDDTQFZ-UHFFFAOYSA-N 1-[3-[4-[6-(bromomethyl)imidazo[1,2-a]pyridin-2-yl]phenyl]pyrazol-1-yl]ethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(=CC=2)C=2N=C3C=CC(CBr)=CN3C=2)=N1 MJRBEDUTDDTQFZ-UHFFFAOYSA-N 0.000 description 3
- XOORWCNTAQNSSW-UHFFFAOYSA-N 1-[4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CN(C=C(F)C=C2)C2=N1 XOORWCNTAQNSSW-UHFFFAOYSA-N 0.000 description 3
- WKEYPPZTEITNHZ-UHFFFAOYSA-N 2-amino-4-bromobenzenethiol Chemical compound NC1=CC(Br)=CC=C1S WKEYPPZTEITNHZ-UHFFFAOYSA-N 0.000 description 3
- LDGHLZFFKMEAOE-UHFFFAOYSA-N 2-amino-5-bromobenzenethiol Chemical compound NC1=CC=C(Br)C=C1S LDGHLZFFKMEAOE-UHFFFAOYSA-N 0.000 description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- MTBLRWFKYSUAKO-MDZDMXLPSA-N (e)-3-(dimethylamino)-1-[4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenyl]prop-2-en-1-one Chemical compound C1=CC(C(=O)/C=C/N(C)C)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 MTBLRWFKYSUAKO-MDZDMXLPSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- YHZRFMKILHIPDQ-UHFFFAOYSA-N 1-[3-[4-[6-[[bis(pyridin-2-ylmethyl)amino]methyl]imidazo[1,2-a]pyridin-2-yl]phenyl]pyrazol-1-yl]ethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(=CC=2)C=2N=C3C=CC(CN(CC=4N=CC=CC=4)CC=4N=CC=CC=4)=CN3C=2)=N1 YHZRFMKILHIPDQ-UHFFFAOYSA-N 0.000 description 2
- IBOCWLNZWLBXEW-UHFFFAOYSA-N 1-[4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CN(C=C(F)C=C2)C2=N1 IBOCWLNZWLBXEW-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- GDXLZBAOBKGCEK-UHFFFAOYSA-N 4-(1,3-oxazol-5-yl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CN=CO1 GDXLZBAOBKGCEK-UHFFFAOYSA-N 0.000 description 2
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 2
- PHXIIAANTPHDQO-UHFFFAOYSA-N 4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)benzonitrile Chemical compound C=1N2C=C(F)C=CC2=NC=1C1=CC=C(C#N)C=C1 PHXIIAANTPHDQO-UHFFFAOYSA-N 0.000 description 2
- FSIRIKFOMQZAIB-UHFFFAOYSA-N 5-[4-(5-iodo-1,3-benzothiazol-2-yl)phenyl]-1,3-oxazole Chemical compound N=1C2=CC(I)=CC=C2SC=1C(C=C1)=CC=C1C1=CN=CO1 FSIRIKFOMQZAIB-UHFFFAOYSA-N 0.000 description 2
- NTBXQZWIMHWGQR-UHFFFAOYSA-N 5-[4-(6-bromo-1,3-benzothiazol-2-yl)phenyl]-1,3-oxazole Chemical compound S1C2=CC(Br)=CC=C2N=C1C(C=C1)=CC=C1C1=CN=CO1 NTBXQZWIMHWGQR-UHFFFAOYSA-N 0.000 description 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [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 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GUJIMWUWNVZSTR-UHFFFAOYSA-N n,n'-bis[2-[(4-methoxyphenyl)methylsulfanyl]-2-methylpropyl]ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CSC(C)(C)CNCCNCC(C)(C)SCC1=CC=C(OC)C=C1 GUJIMWUWNVZSTR-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- XBRVSIPVHYWULW-UHFFFAOYSA-N (3-bromophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(Br)=C1 XBRVSIPVHYWULW-UHFFFAOYSA-N 0.000 description 1
- TXPRFSOGPYITOT-UHFFFAOYSA-N (6-aminopyridin-3-yl)methanol Chemical compound NC1=CC=C(CO)C=N1 TXPRFSOGPYITOT-UHFFFAOYSA-N 0.000 description 1
- WXLXYMRWCBTNAG-MDZDMXLPSA-N (e)-1-[4-(6-bromo-1h-benzimidazol-2-yl)phenyl]-3-(dimethylamino)prop-2-en-1-one Chemical compound C1=CC(C(=O)/C=C/N(C)C)=CC=C1C1=NC2=CC(Br)=CC=C2N1 WXLXYMRWCBTNAG-MDZDMXLPSA-N 0.000 description 1
- DKYBSVJCCUJODM-MDZDMXLPSA-N (e)-3-(dimethylamino)-1-[4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)phenyl]prop-2-en-1-one Chemical compound C1=CC(C(=O)/C=C/N(C)C)=CC=C1C1=CN(C=C(F)C=C2)C2=N1 DKYBSVJCCUJODM-MDZDMXLPSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- GWAYWACDJJZBRL-UHFFFAOYSA-N 1-[2-[4-(1h-pyrazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl]-n,n-bis(pyridin-2-ylmethyl)methanamine Chemical compound C1=CC2=NC(C=3C=CC(=CC=3)C3=NNC=C3)=CN2C=C1CN(CC=1N=CC=CC=1)CC1=CC=CC=N1 GWAYWACDJJZBRL-UHFFFAOYSA-N 0.000 description 1
- GXZPCGYDEWJBHI-UHFFFAOYSA-N 1-[3-[4-[6-(hydroxymethyl)imidazo[1,2-a]pyridin-2-yl]phenyl]pyrazol-1-yl]ethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(=CC=2)C=2N=C3C=CC(CO)=CN3C=2)=N1 GXZPCGYDEWJBHI-UHFFFAOYSA-N 0.000 description 1
- VFWZVGPFTBJVRE-UHFFFAOYSA-N 1-[4-(1-acetylpyrazol-3-yl)phenyl]-2-bromoethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(=CC=2)C(=O)CBr)=N1 VFWZVGPFTBJVRE-UHFFFAOYSA-N 0.000 description 1
- ZRNKSCJSNDRJMW-UHFFFAOYSA-N 1-[4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 ZRNKSCJSNDRJMW-UHFFFAOYSA-N 0.000 description 1
- ZMGMGHNOACSMQN-UHFFFAOYSA-N 1-bromo-3-isothiocyanatobenzene Chemical compound BrC1=CC=CC(N=C=S)=C1 ZMGMGHNOACSMQN-UHFFFAOYSA-N 0.000 description 1
- KXZQYLBVMZGIKC-UHFFFAOYSA-N 1-pyridin-2-yl-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CNCC1=CC=CC=N1 KXZQYLBVMZGIKC-UHFFFAOYSA-N 0.000 description 1
- YDCVSSPRANGNLC-UHFFFAOYSA-N 2-[3-(4-imidazo[1,2-a]pyridin-2-ylphenyl)pyrazol-1-yl]acetic acid Chemical compound OC(=O)CN1C=CC(C=2C=CC(=CC=2)C=2N=C3C=CC=CN3C=2)=N1 YDCVSSPRANGNLC-UHFFFAOYSA-N 0.000 description 1
- DGHVKHMTLBCUAP-UHFFFAOYSA-N 4-(6-fluoroimidazo[1,2-a]pyridin-2-yl)benzaldehyde Chemical compound C=1N2C=C(F)C=CC2=NC=1C1=CC=C(C=O)C=C1 DGHVKHMTLBCUAP-UHFFFAOYSA-N 0.000 description 1
- QKFAADBAQQYFIL-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-2-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN(C=CC=C2)C2=N1 QKFAADBAQQYFIL-UHFFFAOYSA-N 0.000 description 1
- HMLNKRCODQRNPF-UHFFFAOYSA-N 5-[4-(5-bromo-1,3-benzothiazol-2-yl)phenyl]-1,3-oxazole Chemical compound N=1C2=CC(Br)=CC=C2SC=1C(C=C1)=CC=C1C1=CN=CO1 HMLNKRCODQRNPF-UHFFFAOYSA-N 0.000 description 1
- ZPUJTWBWSOOMRP-UHFFFAOYSA-N 5-bromo-1,3-benzothiazol-2-amine Chemical compound BrC1=CC=C2SC(N)=NC2=C1 ZPUJTWBWSOOMRP-UHFFFAOYSA-N 0.000 description 1
- YJTXQLYMECWULH-UHFFFAOYSA-N 5-fluoropyridin-2-amine Chemical compound NC1=CC=C(F)C=N1 YJTXQLYMECWULH-UHFFFAOYSA-N 0.000 description 1
- DBNGJNCAXKNLLQ-UHFFFAOYSA-N 6-[2-[(2-methylpropan-2-yl)oxycarbonyl]hydrazinyl]pyridine-3-carboxylic acid Chemical compound CC(C)(C)OC(=O)NNC1=CC=C(C(O)=O)C=N1 DBNGJNCAXKNLLQ-UHFFFAOYSA-N 0.000 description 1
- VZEBSJIOUMDNLY-UHFFFAOYSA-N 6-bromo-1,3-benzothiazol-2-amine Chemical compound C1=C(Br)C=C2SC(N)=NC2=C1 VZEBSJIOUMDNLY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- MTBLRWFKYSUAKO-UHFFFAOYSA-N C1=CC(C(=O)C=CN(C)C)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 Chemical compound C1=CC(C(=O)C=CN(C)C)=CC=C1C1=CN(C=C(I)C=C2)C2=N1 MTBLRWFKYSUAKO-UHFFFAOYSA-N 0.000 description 1
- WXLXYMRWCBTNAG-UHFFFAOYSA-N C1=CC(C(=O)C=CN(C)C)=CC=C1C1=NC2=CC=C(Br)C=C2N1 Chemical compound C1=CC(C(=O)C=CN(C)C)=CC=C1C1=NC2=CC=C(Br)C=C2N1 WXLXYMRWCBTNAG-UHFFFAOYSA-N 0.000 description 1
- UICJMCPOAZTRSG-UHFFFAOYSA-N CN1N(CC=C1)B1OC(C(O1)(C)C)(C)C Chemical compound CN1N(CC=C1)B1OC(C(O1)(C)C)(C)C UICJMCPOAZTRSG-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- KIUJKTGEKHGSJF-UHFFFAOYSA-N Cl.Cl.N1N=C(C=C1)C1=CC=C(C=C1)C=1N=C2N(C=C(C=C2)NC(C2=CN=C(C=C2)NN)=O)C1 Chemical compound Cl.Cl.N1N=C(C=C1)C1=CC=C(C=C1)C=1N=C2N(C=C(C=C2)NC(C2=CN=C(C=C2)NN)=O)C1 KIUJKTGEKHGSJF-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 210000000692 cap cell Anatomy 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical class [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- FVAUCKIRQBBSSJ-VVUPZWBASA-M sodium;iodine-123(1-) Chemical compound [Na+].[123I-] FVAUCKIRQBBSSJ-VVUPZWBASA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JSGMTEAVJRSNAH-UHFFFAOYSA-N tert-butyl 4-(4-acetylphenyl)pyrazole-1-carboxylate Chemical compound C1=CC(C(=O)C)=CC=C1C1=CN(C(=O)OC(C)(C)C)N=C1 JSGMTEAVJRSNAH-UHFFFAOYSA-N 0.000 description 1
- FIGFBKHPEZKLGS-UHFFFAOYSA-N tert-butyl n-[[5-[(6-aminopyridin-3-yl)carbamoyl]pyridin-2-yl]amino]carbamate Chemical compound C1=NC(NNC(=O)OC(C)(C)C)=CC=C1C(=O)NC1=CC=C(N)N=C1 FIGFBKHPEZKLGS-UHFFFAOYSA-N 0.000 description 1
- BBKRSWPRBKHHMG-UHFFFAOYSA-N tert-butyl n-[[5-[[2-[4-(1-acetylpyrazol-3-yl)phenyl]imidazo[1,2-a]pyridin-6-yl]carbamoyl]pyridin-2-yl]amino]carbamate Chemical compound CC(=O)N1C=CC(C=2C=CC(=CC=2)C=2N=C3C=CC(NC(=O)C=4C=NC(NNC(=O)OC(C)(C)C)=CC=4)=CN3C=2)=N1 BBKRSWPRBKHHMG-UHFFFAOYSA-N 0.000 description 1
- NZBUCABTIWJWAN-UHFFFAOYSA-N tetrabromomethane;triphenylphosphane Chemical compound BrC(Br)(Br)Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NZBUCABTIWJWAN-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008142698A JP4738443B2 (ja) | 2007-05-30 | 2008-05-30 | アミロイドの凝集及び／又は沈着に起因する疾患のイメージング薬及び治療薬 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007143852 | 2007-05-30 | ||
| JP2007143852 | 2007-05-30 | ||
| JP2008142698A JP4738443B2 (ja) | 2007-05-30 | 2008-05-30 | アミロイドの凝集及び／又は沈着に起因する疾患のイメージング薬及び治療薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009007348A JP2009007348A (ja) | 2009-01-15 |
| JP2009007348A5 true JP2009007348A5 (cg-RX-API-DMAC7.html) | 2010-09-30 |
| JP4738443B2 JP4738443B2 (ja) | 2011-08-03 |
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| JP2008142698A Expired - Fee Related JP4738443B2 (ja) | 2007-05-30 | 2008-05-30 | アミロイドの凝集及び／又は沈着に起因する疾患のイメージング薬及び治療薬 |
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| JP (1) | JP4738443B2 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2010128595A1 (ja) * | 2009-05-07 | 2012-11-01 | 富士フイルムＲｉファーマ株式会社 | 放射性ヨウ素標識イミダゾピリジン誘導体の製造法 |
| JP2013256491A (ja) * | 2012-05-14 | 2013-12-26 | Kyoto Univ | 不安定プラークへの選択的集積性に優れる化合物 |
| CN103450111B (zh) * | 2013-09-04 | 2015-07-08 | 温州大学 | 一种苯并噻唑杂环化合物的绿色合成方法 |
| JP6666757B2 (ja) * | 2016-03-10 | 2020-03-18 | 日本メジフィジックス株式会社 | ポリオキシエチレン系非イオン界面活性剤の定量方法及び放射性医薬品製剤の製造方法 |
| JP6831802B2 (ja) * | 2018-01-12 | 2021-02-17 | 上海富吉医療器械有限公司Ｓｈａｎｇｈａｉ Ｃｈａｒｔｗｅｌｌ Ｍｅｄｉｃａｌ Ｉｎｓｔｒｕｍｅｎｔ Ｃｏ．， Ｌｔｄ． | 放射性核種標識化合物及びこれを含有するイメージング剤 |
| CN119841710B (zh) * | 2025-03-21 | 2025-06-03 | 山东飞源新材料有限公司 | 3-氟-1-丙醇的合成方法 |
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