CA2332403A1 - Anti-viral compounds - Google Patents

Info

Publication number

CA2332403A1

CA2332403A1 CA002332403A CA2332403A CA2332403A1 CA 2332403 A1 CA2332403 A1 CA 2332403A1 CA 002332403 A CA002332403 A CA 002332403A CA 2332403 A CA2332403 A CA 2332403A CA 2332403 A1 CA2332403 A1 CA 2332403A1

Authority

CA

Canada

Prior art keywords

mmol

pyridine

product

imidazo

yield

Prior art date

1998-05-20

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 169
• 230000000840 anti-viral effect Effects 0.000 title description 4
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
• -1 CONHOCH3 Chemical group 0.000 claims abstract description 23
• 239000001257 hydrogen Substances 0.000 claims abstract description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 17
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
• 241000700605 Viruses Species 0.000 claims abstract description 12
• 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims abstract description 10
• 101100295741 Gallus gallus COR4 gene Chemical group 0.000 claims abstract description 10
• 101150113676 chr1 gene Proteins 0.000 claims abstract description 10
• 241000709664 Picornaviridae Species 0.000 claims abstract description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
• 125000002541 furyl group Chemical group 0.000 claims abstract description 5
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 9
• 238000000034 method Methods 0.000 claims description 54
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 241000709661 Enterovirus Species 0.000 abstract description 15
• 241000709687 Coxsackievirus Species 0.000 abstract description 4
• 241001466953 Echovirus Species 0.000 abstract description 4
• 241000991587 Enterovirus C Species 0.000 abstract description 4
• 241000710185 Mengo virus Species 0.000 abstract description 3
• 241000710190 Cardiovirus Species 0.000 abstract description 2
• 239000000047 product Substances 0.000 description 357
• 238000002360 preparation method Methods 0.000 description 255
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 154
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 122
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
• 238000005481 NMR spectroscopy Methods 0.000 description 109
• 239000002904 solvent Substances 0.000 description 91
• 239000000243 solution Substances 0.000 description 82
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 80
• 235000019439 ethyl acetate Nutrition 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 67
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 62
• 239000007787 solid Substances 0.000 description 62
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 54
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
• 239000002585 base Substances 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 26
• 239000012267 brine Substances 0.000 description 25
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• 101150041968 CDC13 gene Proteins 0.000 description 22
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 20
• 229940073584 methylene chloride Drugs 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 18
• 238000004440 column chromatography Methods 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 11
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
• 125000000217 alkyl group Chemical group 0.000 description 11
• 239000012300 argon atmosphere Substances 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 239000012312 sodium hydride Substances 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 11
• 238000005160 1H NMR spectroscopy Methods 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000005843 halogen group Chemical group 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 229960001866 silicon dioxide Drugs 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 150000001298 alcohols Chemical class 0.000 description 7
• 229910021529 ammonia Inorganic materials 0.000 description 7
• 239000012065 filter cake Substances 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 6
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
• 150000003568 thioethers Chemical class 0.000 description 6
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 5
• ZALOOIGRDWEGRD-UHFFFAOYSA-N 2-amino-n-methoxy-n-methyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)N(C)OC)C=CC2=NC(N)=C1C1=CC=CC=C1 ZALOOIGRDWEGRD-UHFFFAOYSA-N 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• 229910017974 NH40H Inorganic materials 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000010949 copper Substances 0.000 description 5
• 229910052802 copper Inorganic materials 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 238000001819 mass spectrum Methods 0.000 description 5
• 239000000376 reactant Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 229910052786 argon Inorganic materials 0.000 description 4
• 239000012320 chlorinating reagent Substances 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 230000002140 halogenating effect Effects 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 238000002329 infrared spectrum Methods 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
• 230000002083 iodinating effect Effects 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
• 238000001228 spectrum Methods 0.000 description 4
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
• YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 description 3
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
• LPOCJYNWYIIGNV-UHFFFAOYSA-N 3-phenyl-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C[Si]1(C)CC[Si](C)(C)N1C1=C(C=2C=CC=CC=2)N2C=C(C(O)=O)C=CC2=N1 LPOCJYNWYIIGNV-UHFFFAOYSA-N 0.000 description 3
• FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical group ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• 239000004342 Benzoyl peroxide Substances 0.000 description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• 208000000474 Poliomyelitis Diseases 0.000 description 3
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• LJASNDRCSNYAJQ-UHFFFAOYSA-N [2-amino-3-(2,6-difluorophenyl)imidazo[1,2-a]pyridin-6-yl]-phenylmethanone Chemical compound NC=1N=C2C=CC(C(=O)C=3C=CC=CC=3)=CN2C=1C1=C(F)C=CC=C1F LJASNDRCSNYAJQ-UHFFFAOYSA-N 0.000 description 3
• ALSAFROLRKQEMC-UHFFFAOYSA-N [2-amino-3-(2-methylpropyl)imidazo[1,2-a]pyridin-6-yl]-phenylmethanone Chemical compound C=1N2C(CC(C)C)=C(N)N=C2C=CC=1C(=O)C1=CC=CC=C1 ALSAFROLRKQEMC-UHFFFAOYSA-N 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 230000009435 amidation Effects 0.000 description 3
• 238000007112 amidation reaction Methods 0.000 description 3
• 125000005219 aminonitrile group Chemical group 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 235000019400 benzoyl peroxide Nutrition 0.000 description 3
• 229960003328 benzoyl peroxide Drugs 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
• 229910000024 caesium carbonate Inorganic materials 0.000 description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 238000010265 fast atom bombardment Methods 0.000 description 3
• 239000012091 fetal bovine serum Substances 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 239000003999 initiator Substances 0.000 description 3
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