NO874904L - Fremgangsmaate for fremstilling av nye imidazopyridin-forbindelser. - Google Patents

Info

Publication number

NO874904L

NO874904L NO874904A NO874904A NO874904L NO 874904 L NO874904 L NO 874904L NO 874904 A NO874904 A NO 874904A NO 874904 A NO874904 A NO 874904A NO 874904 L NO874904 L NO 874904L

Authority

NO

Norway

Prior art keywords

alkyl

methyl

hydroxy

compound

nujol

Prior art date

1986-11-26

Links

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• 238000000034 method Methods 0.000 title claims description 48
• 238000002360 preparation method Methods 0.000 title claims description 17
• 150000005232 imidazopyridines Chemical class 0.000 title claims description 6
• -1 amino, carboxy Chemical group 0.000 claims description 327
• 125000000217 alkyl group Chemical group 0.000 claims description 171
• 150000001875 compounds Chemical class 0.000 claims description 103
• 150000003839 salts Chemical class 0.000 claims description 78
• 238000006243 chemical reaction Methods 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 35
• 125000003282 alkyl amino group Chemical group 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
• 125000004423 acyloxy group Chemical group 0.000 claims description 14
• KQBUDLWYGUXLKL-UHFFFAOYSA-N methyl n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C KQBUDLWYGUXLKL-UHFFFAOYSA-N 0.000 claims description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
• 125000005281 alkyl ureido group Chemical group 0.000 claims description 5
• 238000006722 reduction reaction Methods 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• ZTXAFIRXXMEEGM-UHFFFAOYSA-N [3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]thiourea Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1NC(N)=S ZTXAFIRXXMEEGM-UHFFFAOYSA-N 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 2
• 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
• 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
• 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
• 239000000203 mixture Substances 0.000 description 105
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• 235000019441 ethanol Nutrition 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• 238000004519 manufacturing process Methods 0.000 description 42
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• 238000004458 analytical method Methods 0.000 description 31
• 238000002844 melting Methods 0.000 description 30
• 230000008018 melting Effects 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
• 239000002244 precipitate Substances 0.000 description 29
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 238000001914 filtration Methods 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• 229960001701 chloroform Drugs 0.000 description 21
• 238000003756 stirring Methods 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
• 239000002253 acid Substances 0.000 description 16
• 150000002148 esters Chemical group 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• 235000019341 magnesium sulphate Nutrition 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• 125000002252 acyl group Chemical group 0.000 description 14
• 239000007864 aqueous solution Substances 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• 238000000354 decomposition reaction Methods 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 11
• 238000004440 column chromatography Methods 0.000 description 11
• VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 229910052783 alkali metal Inorganic materials 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 235000011054 acetic acid Nutrition 0.000 description 9
• 125000001589 carboacyl group Chemical group 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 125000005907 alkyl ester group Chemical group 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• 229940125904 compound 1 Drugs 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• ADGJCXVQMOKRQE-UHFFFAOYSA-N n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C ADGJCXVQMOKRQE-UHFFFAOYSA-N 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 6
• 208000025865 Ulcer Diseases 0.000 description 6
• BEEWNOMTKNIJGL-UHFFFAOYSA-N [3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]urea Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1NC(N)=O BEEWNOMTKNIJGL-UHFFFAOYSA-N 0.000 description 6
• 230000002411 adverse Effects 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
• LOIHCAGCQVZRTR-UHFFFAOYSA-N (2-amino-6-methylphenyl)methanol Chemical compound CC1=CC=CC(N)=C1CO LOIHCAGCQVZRTR-UHFFFAOYSA-N 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• ZXJRKKGYANTHHA-UHFFFAOYSA-N 3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]aniline Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1N ZXJRKKGYANTHHA-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 150000007530 organic bases Chemical class 0.000 description 5
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 231100000397 ulcer Toxicity 0.000 description 5
• HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
• CPBCJIJRMMTOQX-UHFFFAOYSA-N 1-methyl-1-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]urea Chemical compound NC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C CPBCJIJRMMTOQX-UHFFFAOYSA-N 0.000 description 4
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
• YWJLHGZLQXWELD-UHFFFAOYSA-N 2-hydroxy-n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]propanamide Chemical compound CC(O)C(=O)NC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C YWJLHGZLQXWELD-UHFFFAOYSA-N 0.000 description 4
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• 101150041968 CDC13 gene Proteins 0.000 description 4
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
• 229920000388 Polyphosphate Polymers 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• QEGZTPUGNSANDA-UHFFFAOYSA-N n,3-dimethyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]aniline Chemical compound CNC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C QEGZTPUGNSANDA-UHFFFAOYSA-N 0.000 description 4
• WBNCISBNSPYRTH-UHFFFAOYSA-N n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]-2-oxopropanamide Chemical compound CC(=O)C(=O)NC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C WBNCISBNSPYRTH-UHFFFAOYSA-N 0.000 description 4
• DCXRXQZZHPKDMX-UHFFFAOYSA-N n-[[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]carbamothioyl]benzamide Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1NC(=S)NC(=O)C1=CC=CC=C1 DCXRXQZZHPKDMX-UHFFFAOYSA-N 0.000 description 4
• KZZKGLMQESJFBH-UHFFFAOYSA-N n-methyl-n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]acetamide Chemical compound CC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C KZZKGLMQESJFBH-UHFFFAOYSA-N 0.000 description 4
• CLIAUTMYZJGKCR-UHFFFAOYSA-N n-methyl-n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C CLIAUTMYZJGKCR-UHFFFAOYSA-N 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
• 239000001205 polyphosphate Substances 0.000 description 4
• 235000011176 polyphosphates Nutrition 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• RJXUXFXGPKIDJQ-UHFFFAOYSA-N tert-butyl n-[2-[[(2-methylphenyl)-(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]amino]-2-oxoethyl]carbamate Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OC(NC(=O)CNC(=O)OC(C)(C)C)C1=CC=CC=C1C RJXUXFXGPKIDJQ-UHFFFAOYSA-N 0.000 description 4
• GABFMVHXIKDNBE-UHFFFAOYSA-N tert-butyl n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]carbamate Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1NC(=O)OC(C)(C)C GABFMVHXIKDNBE-UHFFFAOYSA-N 0.000 description 4
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• HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
• YRAIRTVWWCOPOK-UHFFFAOYSA-N methyl n-[2-(chloromethyl)-3-methylphenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC=CC(C)=C1CCl YRAIRTVWWCOPOK-UHFFFAOYSA-N 0.000 description 1
• DSEJVTAYKLSYLG-UHFFFAOYSA-N methyl n-[2-(chloromethyl)phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1CCl DSEJVTAYKLSYLG-UHFFFAOYSA-N 0.000 description 1
• NFBDOMVFORFWCR-UHFFFAOYSA-N methyl n-[2-[(2-amino-6-methylpyridin-3-yl)oxymethyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1COC1=CC=C(C)N=C1N NFBDOMVFORFWCR-UHFFFAOYSA-N 0.000 description 1
• OTYWRPBTJWHYON-UHFFFAOYSA-N methyl n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1N OTYWRPBTJWHYON-UHFFFAOYSA-N 0.000 description 1
• ANXDCSNUPYIBML-UHFFFAOYSA-N methyl n-[2-[(2-aminopyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1COC1=CC=CN=C1N ANXDCSNUPYIBML-UHFFFAOYSA-N 0.000 description 1
• QBQUZULUWDPYDQ-UHFFFAOYSA-N methyl n-[2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1COC1=CC=CN=C1[N+]([O-])=O QBQUZULUWDPYDQ-UHFFFAOYSA-N 0.000 description 1
• LJPITJJUODAEQC-UHFFFAOYSA-N methyl n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]carbamate;sulfuric acid Chemical compound OS(O)(=O)=O.COC(=O)NC1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C LJPITJJUODAEQC-UHFFFAOYSA-N 0.000 description 1
• AODAZXZEOJUXNI-UHFFFAOYSA-N methyl n-[[2-[(2-aminopyridin-3-yl)oxymethyl]phenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC=CC=C1COC1=CC=CN=C1N AODAZXZEOJUXNI-UHFFFAOYSA-N 0.000 description 1
• AFKIJAQKEVUYQP-UHFFFAOYSA-N methyl n-[[2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]methyl]carbamate Chemical compound COC(=O)NCC1=CC=CC=C1COC1=CC=CN=C1[N+]([O-])=O AFKIJAQKEVUYQP-UHFFFAOYSA-N 0.000 description 1
• BINBJKKMZAHPED-UHFFFAOYSA-N methyl n-methyl-n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound COC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1[N+]([O-])=O BINBJKKMZAHPED-UHFFFAOYSA-N 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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• URLYFAPQZQNYHX-UHFFFAOYSA-N n,n-dimethyl-1-[2-methyl-8-[(2-nitrophenyl)methoxy]imidazo[1,2-a]pyridin-3-yl]methanamine Chemical compound C=1C=CN2C(CN(C)C)=C(C)N=C2C=1OCC1=CC=CC=C1[N+]([O-])=O URLYFAPQZQNYHX-UHFFFAOYSA-N 0.000 description 1
• VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
• OQWBSIMVDHAYEQ-UHFFFAOYSA-N n-(4-formyl-3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C=O)C(C)=C1 OQWBSIMVDHAYEQ-UHFFFAOYSA-N 0.000 description 1
• WTOAMNUITVYGFT-UHFFFAOYSA-N n-[(2-aminopyridin-3-yl)oxy-(2-methylphenyl)methyl]-2-hydroxyacetamide Chemical compound CC1=CC=CC=C1C(NC(=O)CO)OC1=CC=CN=C1N WTOAMNUITVYGFT-UHFFFAOYSA-N 0.000 description 1
• LYKWUPAAUZIAAA-UHFFFAOYSA-N n-[2-(chloromethyl)-3-methylphenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C)=C1CCl LYKWUPAAUZIAAA-UHFFFAOYSA-N 0.000 description 1
• GFAFQSQABQVTDQ-UHFFFAOYSA-N n-[2-(chloromethyl)-3-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C)=C1CCl GFAFQSQABQVTDQ-UHFFFAOYSA-N 0.000 description 1
• DQTGOZMADUKGQE-UHFFFAOYSA-N n-[2-(chloromethyl)-3-methylphenyl]formamide Chemical compound CC1=CC=CC(NC=O)=C1CCl DQTGOZMADUKGQE-UHFFFAOYSA-N 0.000 description 1
• OLZSJTUUPPLLJD-UHFFFAOYSA-N n-[2-(chloromethyl)-3-methylphenyl]methanesulfonamide Chemical compound CC1=CC=CC(NS(C)(=O)=O)=C1CCl OLZSJTUUPPLLJD-UHFFFAOYSA-N 0.000 description 1
• XEPDVUIEOCWRBJ-UHFFFAOYSA-N n-[2-(chloromethyl)-3-methylphenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(C)=C1CCl XEPDVUIEOCWRBJ-UHFFFAOYSA-N 0.000 description 1
• WKVBPRDIWSTGKG-UHFFFAOYSA-N n-[2-(chloromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1CCl WKVBPRDIWSTGKG-UHFFFAOYSA-N 0.000 description 1
• RYVSEYVJNPCJER-UHFFFAOYSA-N n-[2-(hydroxymethyl)-3-methylphenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C)=C1CO RYVSEYVJNPCJER-UHFFFAOYSA-N 0.000 description 1
• RQJHQXMAFMCVHL-UHFFFAOYSA-N n-[2-(hydroxymethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1CO RQJHQXMAFMCVHL-UHFFFAOYSA-N 0.000 description 1
• OKMDHCPECPRTNV-UHFFFAOYSA-N n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1N OKMDHCPECPRTNV-UHFFFAOYSA-N 0.000 description 1
• MIWNHXDTROAWNK-UHFFFAOYSA-N n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(C)=C1COC1=CC=CN=C1N MIWNHXDTROAWNK-UHFFFAOYSA-N 0.000 description 1
• RCISJIRCDMETBW-UHFFFAOYSA-N n-[2-[(2-aminopyridin-3-yl)oxymethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1COC1=CC=CN=C1N RCISJIRCDMETBW-UHFFFAOYSA-N 0.000 description 1
• SZVUJTIJCMLLAF-UHFFFAOYSA-N n-[2-[(2-aminopyridin-3-yl)oxymethyl]phenyl]formamide Chemical compound NC1=NC=CC=C1OCC1=CC=CC=C1NC=O SZVUJTIJCMLLAF-UHFFFAOYSA-N 0.000 description 1
• CUVIOVFYNVXSQJ-UHFFFAOYSA-N n-[2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1COC1=CC=CN=C1[N+]([O-])=O CUVIOVFYNVXSQJ-UHFFFAOYSA-N 0.000 description 1
• AGXZWRGHCFHKMD-UHFFFAOYSA-N n-[2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]formamide Chemical compound [O-][N+](=O)C1=NC=CC=C1OCC1=CC=CC=C1NC=O AGXZWRGHCFHKMD-UHFFFAOYSA-N 0.000 description 1
• GQTYOBNDBVHAKW-UHFFFAOYSA-N n-[2-[[3-[(dimethylamino)methyl]-2-methylimidazo[1,2-a]pyridin-8-yl]oxymethyl]phenyl]acetamide Chemical compound C=1C=CN2C(CN(C)C)=C(C)N=C2C=1OCC1=CC=CC=C1NC(C)=O GQTYOBNDBVHAKW-UHFFFAOYSA-N 0.000 description 1
• ZECRJPPLWBQCEY-UHFFFAOYSA-N n-[3-(chloromethyl)-2-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CCl)=C1C ZECRJPPLWBQCEY-UHFFFAOYSA-N 0.000 description 1
• KMNOKPLNZUYGKM-UHFFFAOYSA-N n-[3-(chloromethyl)-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(CCl)=C1 KMNOKPLNZUYGKM-UHFFFAOYSA-N 0.000 description 1
• CHGVURZJZWKXBU-UHFFFAOYSA-N n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(C)=C1COC1=CC=CN=C1[N+]([O-])=O CHGVURZJZWKXBU-UHFFFAOYSA-N 0.000 description 1
• JKJIWIKVEGIPRU-UHFFFAOYSA-N n-[4-(chloromethyl)-3-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CCl)C(C)=C1 JKJIWIKVEGIPRU-UHFFFAOYSA-N 0.000 description 1
• LUGUYMHBKVWFQP-UHFFFAOYSA-N n-[4-(hydroxymethyl)-3-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CO)C(C)=C1 LUGUYMHBKVWFQP-UHFFFAOYSA-N 0.000 description 1
• YHNFIVMWZGGLFI-UHFFFAOYSA-N n-[4-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]acetamide Chemical compound CC1=CC(NC(=O)C)=CC=C1COC1=CC=CN=C1N YHNFIVMWZGGLFI-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• IGMJWXIFGIUILG-UHFFFAOYSA-N n-methyl-n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1[N+]([O-])=O IGMJWXIFGIUILG-UHFFFAOYSA-N 0.000 description 1
• 229910000480 nickel oxide Inorganic materials 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
• HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
• 229910003445 palladium oxide Inorganic materials 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 229960003975 potassium Drugs 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
• QFRLYXMFFHKQCB-UHFFFAOYSA-N propan-2-yl n-[2-(chloromethyl)-3-methylphenyl]carbamate Chemical compound CC(C)OC(=O)NC1=CC=CC(C)=C1CCl QFRLYXMFFHKQCB-UHFFFAOYSA-N 0.000 description 1
• UEQHBGALECSIOY-UHFFFAOYSA-N propan-2-yl n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]carbamate Chemical compound CC(C)OC(=O)NC1=CC=CC(C)=C1COC1=CC=CN=C1N UEQHBGALECSIOY-UHFFFAOYSA-N 0.000 description 1
• CETOUBFITLUDIS-UHFFFAOYSA-N propan-2-yl n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound CC(C)OC(=O)NC1=CC=CC(C)=C1COC1=CC=CN=C1[N+]([O-])=O CETOUBFITLUDIS-UHFFFAOYSA-N 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000001308 pyruvoyl group Chemical group O=C([*])C(=O)C([H])([H])[H] 0.000 description 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 238000012453 sprague-dawley rat model Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• BBTIVSJGUKSEAK-UHFFFAOYSA-N tert-butyl n-[2-(chloromethyl)-3-methylphenyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(C)=C1CCl BBTIVSJGUKSEAK-UHFFFAOYSA-N 0.000 description 1
• DASHHAJXFSJHIG-UHFFFAOYSA-N tert-butyl n-[2-(chloromethyl)-3-methylphenyl]carbamate Chemical compound CC1=CC=CC(NC(=O)OC(C)(C)C)=C1CCl DASHHAJXFSJHIG-UHFFFAOYSA-N 0.000 description 1
• SNJUBSOZJQWQNT-UHFFFAOYSA-N tert-butyl n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1N SNJUBSOZJQWQNT-UHFFFAOYSA-N 0.000 description 1
• GEESJPHFVSHANQ-UHFFFAOYSA-N tert-butyl n-[2-[(2-aminopyridin-3-yl)oxymethyl]-3-methylphenyl]carbamate Chemical compound CC1=CC=CC(NC(=O)OC(C)(C)C)=C1COC1=CC=CN=C1N GEESJPHFVSHANQ-UHFFFAOYSA-N 0.000 description 1
• RXZANMFIVLXSOK-UHFFFAOYSA-N tert-butyl n-[2-[[(2-aminopyridin-3-yl)oxy-(2-methylphenyl)methyl]amino]-2-oxoethyl]carbamate Chemical compound CC1=CC=CC=C1C(NC(=O)CNC(=O)OC(C)(C)C)OC1=CC=CN=C1N RXZANMFIVLXSOK-UHFFFAOYSA-N 0.000 description 1
• IZLMNJZCELCDHA-UHFFFAOYSA-N tert-butyl n-[2-[[(2-methylphenyl)-(2-nitropyridin-3-yl)oxymethyl]amino]-2-oxoethyl]carbamate Chemical compound CC1=CC=CC=C1C(NC(=O)CNC(=O)OC(C)(C)C)OC1=CC=CN=C1[N+]([O-])=O IZLMNJZCELCDHA-UHFFFAOYSA-N 0.000 description 1
• HWSNBOZVWWBLFM-UHFFFAOYSA-N tert-butyl n-[2-[[chloro-(2-methylphenyl)methyl]amino]-2-oxoethyl]carbamate Chemical compound CC1=CC=CC=C1C(Cl)NC(=O)CNC(=O)OC(C)(C)C HWSNBOZVWWBLFM-UHFFFAOYSA-N 0.000 description 1
• HDYIKBGHQGTPJW-UHFFFAOYSA-N tert-butyl n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound CC1=CC=CC(NC(=O)OC(C)(C)C)=C1COC1=CC=CN=C1[N+]([O-])=O HDYIKBGHQGTPJW-UHFFFAOYSA-N 0.000 description 1
• KCTQGBWDNFLVGQ-UHFFFAOYSA-N tert-butyl n-methyl-n-[3-methyl-2-[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)oxymethyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN2C1=NC(C)=C2CC#C KCTQGBWDNFLVGQ-UHFFFAOYSA-N 0.000 description 1
• UQTYDEQDLBFBRS-UHFFFAOYSA-N tert-butyl n-methyl-n-[3-methyl-2-[(2-nitropyridin-3-yl)oxymethyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(C)=C1COC1=CC=CN=C1[N+]([O-])=O UQTYDEQDLBFBRS-UHFFFAOYSA-N 0.000 description 1
• 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 229910052718 tin Inorganic materials 0.000 description 1
• 239000011135 tin Substances 0.000 description 1
• 125000005425 toluyl group Chemical group 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 125000005270 trialkylamine group Chemical group 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
• 230000036269 ulceration Effects 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
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