NO862208L - Fremgangsmaate fpr fremstilling av heterocykliske forbindelser. - Google Patents
Fremgangsmaate fpr fremstilling av heterocykliske forbindelser.Info
- Publication number
- NO862208L NO862208L NO862208A NO862208A NO862208L NO 862208 L NO862208 L NO 862208L NO 862208 A NO862208 A NO 862208A NO 862208 A NO862208 A NO 862208A NO 862208 L NO862208 L NO 862208L
- Authority
- NO
- Norway
- Prior art keywords
- pyridine
- methylimidazo
- propynyl
- denotes
- propynyloxymethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 86
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 25
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- -1 1,2-propadienyl Chemical group 0.000 claims description 196
- 239000002253 acid Substances 0.000 claims description 11
- 230000001955 cumulated effect Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- JHZSCMMCPSPAQU-UHFFFAOYSA-N 2-methyl-8-[(2-methylphenyl)methoxy]-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC=C1C JHZSCMMCPSPAQU-UHFFFAOYSA-N 0.000 claims description 4
- GXLLBDISHZFBDZ-UHFFFAOYSA-N 2-methyl-8-[(2-methylphenyl)methoxy]-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1C GXLLBDISHZFBDZ-UHFFFAOYSA-N 0.000 claims description 4
- JTNAGYCFQPWDNX-UHFFFAOYSA-N 2-methyl-8-phenylmethoxy-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC=C1 JTNAGYCFQPWDNX-UHFFFAOYSA-N 0.000 claims description 4
- IVBUOMZMCXXDST-UHFFFAOYSA-N 4-[(2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl)methoxy]but-2-ynoic acid Chemical compound C=1C=CN2C(COCC#CC(O)=O)=C(C)N=C2C=1OCC1=CC=CC=C1 IVBUOMZMCXXDST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- ZLFOBGQONQUHNZ-UHFFFAOYSA-N ethyl 4-[(2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl)methoxy]but-2-ynoate Chemical compound C=1C=CN2C(COCC#CC(=O)OCC)=C(C)N=C2C=1OCC1=CC=CC=C1 ZLFOBGQONQUHNZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- DQOLHAGPFLUSBQ-UHFFFAOYSA-N 2-methyl-n-[(2-methylphenyl)methyl]-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridin-8-amine;hydrochloride Chemical compound Cl.C=1C=CN2C(COCC#C)=C(C)N=C2C=1NCC1=CC=CC=C1C DQOLHAGPFLUSBQ-UHFFFAOYSA-N 0.000 claims description 3
- QDTCDBIDBHQZCB-UHFFFAOYSA-N 2-phenyl-8-phenylmethoxy-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C=3C=CC=CC=3)N=C2C=1OCC1=CC=CC=C1 QDTCDBIDBHQZCB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- XAWOQASDAMIVSS-UHFFFAOYSA-N 8-[(2-chlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC=C1Cl XAWOQASDAMIVSS-UHFFFAOYSA-N 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- BYKMLAYXQJANGR-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridin-8-amine;hydrochloride Chemical compound Cl.C=1C=CN2C(COCC#C)=C(C)N=C2C=1NCC1=CC=CC=C1Cl BYKMLAYXQJANGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- CWHMMWKYKXTABB-UHFFFAOYSA-N 2-methyl-3-prop-2-ynyl-8-(1,2,3,4-tetrahydronaphthalen-1-yloxy)imidazo[1,2-a]pyridine Chemical compound C1CCC2=CC=CC=C2C1OC1=CC=CN2C1=NC(C)=C2CC#C CWHMMWKYKXTABB-UHFFFAOYSA-N 0.000 claims description 2
- ONZRMGKVFCHDBW-UHFFFAOYSA-N 2-methyl-8-(1-phenylethoxy)-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OC(C)C1=CC=CC=C1 ONZRMGKVFCHDBW-UHFFFAOYSA-N 0.000 claims description 2
- DCPSLJPTDVMHPS-UHFFFAOYSA-N 2-methyl-8-(2-phenylethoxy)-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCCC1=CC=CC=C1 DCPSLJPTDVMHPS-UHFFFAOYSA-N 0.000 claims description 2
- UAKHNHOWWGXLER-UHFFFAOYSA-N 2-methyl-8-(3-phenylprop-2-enoxy)-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC=CC1=CC=CC=C1 UAKHNHOWWGXLER-UHFFFAOYSA-N 0.000 claims description 2
- SCHNOQKIVSIFOK-UHFFFAOYSA-N 2-methyl-8-[(2-methylphenyl)methoxy]-3-prop-2-ynylimidazo[1,2-a]pyrazine Chemical compound N=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1C SCHNOQKIVSIFOK-UHFFFAOYSA-N 0.000 claims description 2
- FXFGJFJQWJFARO-UHFFFAOYSA-N 2-methyl-8-[(2-methylphenyl)methoxy]-3-propa-1,2-dienylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(C=C=C)=C(C)N=C2C=1OCC1=CC=CC=C1C FXFGJFJQWJFARO-UHFFFAOYSA-N 0.000 claims description 2
- KXTGBBYGVPIXMF-UHFFFAOYSA-N 2-methyl-8-[(2-propan-2-ylphenyl)methoxy]-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound CC(C)C1=CC=CC=C1COC1=CC=CN2C1=NC(C)=C2CC#C KXTGBBYGVPIXMF-UHFFFAOYSA-N 0.000 claims description 2
- LKVJJMIPZDWAJE-UHFFFAOYSA-N 2-methyl-8-phenylmethoxy-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine;hydrochloride Chemical compound Cl.C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC=C1 LKVJJMIPZDWAJE-UHFFFAOYSA-N 0.000 claims description 2
- YXYBCNLQSBPGFS-UHFFFAOYSA-N 2-methyl-8-phenylmethoxy-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1 YXYBCNLQSBPGFS-UHFFFAOYSA-N 0.000 claims description 2
- NCLKUOQZTCNTDU-UHFFFAOYSA-N 2-methyl-n-[(2-methylphenyl)methyl]-3-prop-2-ynylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=CC=CC=C1C NCLKUOQZTCNTDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- SEGQEMSKIQEDEV-UHFFFAOYSA-N 8-(cyclohexylmethoxy)-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1CCCCC1 SEGQEMSKIQEDEV-UHFFFAOYSA-N 0.000 claims description 2
- DMBCWUTVXSRXKX-UHFFFAOYSA-N 8-[(2,4-dichlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=C(Cl)C=C1Cl DMBCWUTVXSRXKX-UHFFFAOYSA-N 0.000 claims description 2
- NKSWYNHSBIUZFE-UHFFFAOYSA-N 8-[(2,6-dichlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=C(Cl)C=CC=C1Cl NKSWYNHSBIUZFE-UHFFFAOYSA-N 0.000 claims description 2
- XWDUMCRKGJHPPB-UHFFFAOYSA-N 8-[(2,6-dichlorophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(Cl)C=CC=C1Cl XWDUMCRKGJHPPB-UHFFFAOYSA-N 0.000 claims description 2
- HKCZRTFNSUWRAS-UHFFFAOYSA-N 8-[(2,6-dimethylphenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=C(C)C=CC=C1C HKCZRTFNSUWRAS-UHFFFAOYSA-N 0.000 claims description 2
- DBKSZNJBTMGIJD-UHFFFAOYSA-N 8-[(2-bromophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC=C1Br DBKSZNJBTMGIJD-UHFFFAOYSA-N 0.000 claims description 2
- NPXSUACQUZNRMS-UHFFFAOYSA-N 8-[(2-bromophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1Br NPXSUACQUZNRMS-UHFFFAOYSA-N 0.000 claims description 2
- WNNQBOZNLFWIPZ-UHFFFAOYSA-N 8-[(2-chlorophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1Cl WNNQBOZNLFWIPZ-UHFFFAOYSA-N 0.000 claims description 2
- BLQRQMBYSXYZJU-UHFFFAOYSA-N 8-[(2-ethylphenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound CCC1=CC=CC=C1COC1=CC=CN2C1=NC(C)=C2CC#C BLQRQMBYSXYZJU-UHFFFAOYSA-N 0.000 claims description 2
- WGEDIXKHJJUPIX-UHFFFAOYSA-N 8-[(2-fluorophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC=C1F WGEDIXKHJJUPIX-UHFFFAOYSA-N 0.000 claims description 2
- WXVLMKNMVCBRGC-UHFFFAOYSA-N 8-[(3,4-dichlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=C(Cl)C(Cl)=C1 WXVLMKNMVCBRGC-UHFFFAOYSA-N 0.000 claims description 2
- OMSJHGWPDPZCEF-UHFFFAOYSA-N 8-[(3-chlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=CC(Cl)=C1 OMSJHGWPDPZCEF-UHFFFAOYSA-N 0.000 claims description 2
- MHYZFVMXPXQIEH-UHFFFAOYSA-N 8-[(3-chlorophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=CC(Cl)=C1 MHYZFVMXPXQIEH-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWCLPLBBJNK-UHFFFAOYSA-N 8-[(4-chlorophenyl)methoxy]-2-methyl-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=C(C)N=C2C=1OCC1=CC=C(Cl)C=C1 ONIBWCLPLBBJNK-UHFFFAOYSA-N 0.000 claims description 2
- ZPBXYBCIXAHQPS-UHFFFAOYSA-N 8-[(4-chlorophenyl)methoxy]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1OCC1=CC=C(Cl)C=C1 ZPBXYBCIXAHQPS-UHFFFAOYSA-N 0.000 claims description 2
- XLJRTXHIGCHPEN-UHFFFAOYSA-N 8-ethoxy-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine Chemical compound CCOC1=CC=CN2C(CC#C)=C(C)N=C12 XLJRTXHIGCHPEN-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- GMIFAIOYCVDKMI-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=CC=CC=C1Cl GMIFAIOYCVDKMI-UHFFFAOYSA-N 0.000 claims description 2
- VQLGUOHPDJGLJV-UHFFFAOYSA-N 2-methyl-n-[(2-methylphenyl)methyl]-3-prop-2-ynylimidazo[1,2-a]pyrazin-8-amine Chemical compound N=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=CC=CC=C1C VQLGUOHPDJGLJV-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 238000002844 melting Methods 0.000 description 89
- 230000008018 melting Effects 0.000 description 89
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 86
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000002329 infrared spectrum Methods 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 20
- 238000000354 decomposition reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WYGLCSFHIBLIKZ-UHFFFAOYSA-N 2-oxohex-5-yn-3-yl methanesulfonate Chemical compound C#CCC(C(=O)C)OS(C)(=O)=O WYGLCSFHIBLIKZ-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 206010052428 Wound Diseases 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
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- ITBZZBXSPXZGDJ-UHFFFAOYSA-N 8-[(3-chlorophenyl)methoxy]-2-methylimidazo[1,2-a]pyridine Chemical compound C12=NC(C)=CN2C=CC=C1OCC1=CC=CC(Cl)=C1 ITBZZBXSPXZGDJ-UHFFFAOYSA-N 0.000 description 1
- DYFVERDTBSQGMV-UHFFFAOYSA-N 8-phenylmethoxy-3-(prop-2-ynoxymethyl)imidazo[1,2-a]pyridine Chemical compound C=1C=CN2C(COCC#C)=CN=C2C=1OCC1=CC=CC=C1 DYFVERDTBSQGMV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UZWJCFAOGQSCDP-UHFFFAOYSA-N n,n-dimethyl-1-(2-phenyl-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl)methanamine Chemical compound C=1C=CN2C(CN(C)C)=C(C=3C=CC=CC=3)N=C2C=1OCC1=CC=CC=C1 UZWJCFAOGQSCDP-UHFFFAOYSA-N 0.000 description 1
- ASAFSRWCSVESKG-UHFFFAOYSA-N n,n-dimethyl-1-(8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl)methanamine Chemical compound C=1C=CN2C(CN(C)C)=CN=C2C=1OCC1=CC=CC=C1 ASAFSRWCSVESKG-UHFFFAOYSA-N 0.000 description 1
- NWNRGKTXDMUNGO-UHFFFAOYSA-N n,n-dimethyl-1-[2-methyl-8-(1-phenylethoxy)imidazo[1,2-a]pyridin-3-yl]methanamine Chemical compound C=1C=CN2C(CN(C)C)=C(C)N=C2C=1OC(C)C1=CC=CC=C1 NWNRGKTXDMUNGO-UHFFFAOYSA-N 0.000 description 1
- LQLGTVMZZOOFMP-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-methylimidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C)=CN2C=CC=C1NCC1=CC=CC=C1Cl LQLGTVMZZOOFMP-UHFFFAOYSA-N 0.000 description 1
- FGOFICWDOKHOSI-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-3-[(dimethylamino)methyl]-2-methylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C=CN2C(CN(C)C)=C(C)N=C2C=1NCC1=CC=CC=C1Cl FGOFICWDOKHOSI-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 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
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858514080A GB8514080D0 (en) | 1985-06-04 | 1985-06-04 | Imidazopyridine compounds |
| GB858530878A GB8530878D0 (en) | 1985-12-16 | 1985-12-16 | Imidazopyridine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO862208D0 NO862208D0 (no) | 1986-06-03 |
| NO862208L true NO862208L (no) | 1986-12-05 |
Family
ID=26289330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862208A NO862208L (no) | 1985-06-04 | 1986-06-03 | Fremgangsmaate fpr fremstilling av heterocykliske forbindelser. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4725601A (zh) |
| EP (1) | EP0204285B1 (zh) |
| KR (1) | KR870000332A (zh) |
| CN (1) | CN86104313A (zh) |
| AT (1) | ATE71625T1 (zh) |
| AU (1) | AU593802B2 (zh) |
| CA (1) | CA1257264A (zh) |
| DE (1) | DE3683403D1 (zh) |
| DK (1) | DK250386A (zh) |
| ES (1) | ES8800943A1 (zh) |
| FI (1) | FI862210A (zh) |
| GR (1) | GR861379B (zh) |
| HU (1) | HUT40798A (zh) |
| IL (1) | IL78923A0 (zh) |
| NO (1) | NO862208L (zh) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831041A (en) * | 1986-11-26 | 1989-05-16 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
| IL86269A0 (en) * | 1987-05-08 | 1988-11-15 | Byk Gulden Lomberg Chem Fab | Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| EP0370056A1 (de) * | 1987-07-16 | 1990-05-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Neue diazole |
| GB8722488D0 (en) * | 1987-09-24 | 1987-10-28 | Fujisawa Pharmaceutical Co | Imidazopyridine compound |
| AT390438B (de) * | 1987-10-08 | 1990-05-10 | Yamanouchi Pharma Co Ltd | Neue imidazo(1,2-a)pyridinderivate und deren herstellung und diese enthaltende pharmazeutische zubereitungen |
| SE8704248D0 (sv) * | 1987-10-30 | 1987-10-30 | Haessle Ab | Medical use |
| EP0368158A1 (de) * | 1988-11-07 | 1990-05-16 | Byk Gulden Lomberg Chemische Fabrik GmbH | Neue Imidazopyridine |
| DE3837809A1 (de) * | 1988-11-08 | 1990-05-10 | Merck Patent Gmbh | Tetralinderivate |
| GB9201693D0 (en) * | 1992-01-27 | 1992-03-11 | Smithkline Beecham Intercredit | Compounds |
| US5574042A (en) * | 1992-11-02 | 1996-11-12 | Fujisawa Pharmaceutical Co., Ltd | Imidazo [1,2-a] pyridines and their pharmaceutical use |
| UA48122C2 (uk) * | 1993-10-11 | 2002-08-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ |
| RU2138501C1 (ru) * | 1994-07-28 | 1999-09-27 | Бык Гульден Ломберг Хемише Фабрик Гмбх | Имидазопиридиназолидиноны, их соли и лекарственное средство |
| CN1064360C (zh) * | 1995-04-21 | 2001-04-11 | 新日本药品株式会社 | 稠合咪唑并[1,2－a]吡啶类 |
| US6992188B1 (en) | 1995-12-08 | 2006-01-31 | Pfizer, Inc. | Substituted heterocyclic derivatives |
| ES2200039T3 (es) * | 1995-12-08 | 2004-03-01 | Pfizer Inc. | Derivados heterociclicos sustituidos como antagonistas de crf. |
| WO1997027192A1 (de) * | 1996-01-26 | 1997-07-31 | Byk Gulden Lomberg Chemische Fabrik Gmbh | 3-methylimidazopyridine |
| AU1545297A (en) * | 1996-01-26 | 1997-08-20 | Byk Gulden | Imidazopyridine halides |
| SE9700661D0 (sv) | 1997-02-25 | 1997-02-25 | Astra Ab | New compounds |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| SE9801526D0 (sv) * | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| SE9802793D0 (sv) | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
| SE9802794D0 (sv) * | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
| CA2311483A1 (en) * | 2000-06-12 | 2001-12-12 | Gregory N Beatch | IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF |
| SE0003186D0 (sv) * | 2000-09-07 | 2000-09-07 | Astrazeneca Ab | New process |
| US6900324B2 (en) | 2000-09-07 | 2005-05-31 | Astrazeneca Ab | Process for preparing a substituted imidazopyridine compound |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| SE0102808D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | New compounds |
| DE10145457A1 (de) | 2001-09-14 | 2003-04-03 | Basf Ag | Substituierte Imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-one, Verfahren zu ihrer Herstellung, sowie deren Verwendung zur Herstellung von Imidazo[1,2,-a]pyridinen |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| AR043002A1 (es) * | 2003-02-18 | 2005-07-13 | Altana Pharma Ag | Imidazopirazinas 6-substituidos |
| JP4695588B2 (ja) | 2003-02-26 | 2011-06-08 | スージェン， インク． | プロテインキナーゼ阻害剤としてのアミノヘテロアリール化合物 |
| US7470791B2 (en) | 2003-03-10 | 2008-12-30 | Nycomed Gmbh | Process for the preparation of roflumilast |
| SE0301904D0 (sv) * | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound II with therapeutic effect |
| CN1874772A (zh) | 2003-11-03 | 2006-12-06 | 阿斯利康(瑞典)有限公司 | 治疗隐匿性胃食管反流的咪唑并[1,2－a]吡啶衍生物 |
| JP2008523139A (ja) * | 2004-12-14 | 2008-07-03 | アストラゼネカ・アクチエボラーグ | 置換アミノピリジン類及びその使用 |
| CA2601250C (en) * | 2005-03-16 | 2014-10-28 | Nycomed Gmbh | Taste masked dosage form containing roflumilast |
| CA2620223A1 (en) | 2005-09-02 | 2007-03-08 | Abbott Laboratories | Novel imidazo based heterocycles |
| CN101326175B (zh) | 2005-12-05 | 2012-07-18 | 辉瑞产品公司 | C-met/hgfr抑制剂的多晶型物 |
| BRPI0619424B1 (pt) | 2005-12-05 | 2022-02-08 | Pfizer Products Inc | Uso de inibidores c-met/hgfrs para a fabricação de medicamentos |
| MX2008015747A (es) * | 2006-06-06 | 2008-12-19 | Schering Corp | Imidazopirazinas como inhibidores de la proteina quinasa. |
| TW200815447A (en) * | 2006-06-14 | 2008-04-01 | Astrazeneca Ab | Novel compounds IV |
| US20080051420A1 (en) * | 2006-06-14 | 2008-02-28 | Astrazeneca Ab | New Compounds 317 |
| FI20086158A0 (fi) | 2008-12-03 | 2008-12-03 | Mikael Dahlstroem | Imidatsopyridiinijohdannaiset |
| JP5458813B2 (ja) * | 2009-11-10 | 2014-04-02 | オムロン株式会社 | 光電センサ |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| US4507294A (en) * | 1982-03-08 | 1985-03-26 | Schering Corp. | Imidazo[1,2-a]pyrazines |
| DE3269604D1 (en) * | 1981-06-26 | 1986-04-10 | Schering Corp | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
| AU7928787A (en) * | 1986-10-07 | 1988-04-14 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| US4831041A (en) * | 1986-11-26 | 1989-05-16 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
-
1986
- 1986-05-21 US US06/865,331 patent/US4725601A/en not_active Expired - Fee Related
- 1986-05-26 FI FI862210A patent/FI862210A/fi not_active Application Discontinuation
- 1986-05-27 IL IL78923A patent/IL78923A0/xx unknown
- 1986-05-28 DK DK250386A patent/DK250386A/da not_active Application Discontinuation
- 1986-05-28 GR GR861379A patent/GR861379B/el unknown
- 1986-05-30 CA CA000510496A patent/CA1257264A/en not_active Expired
- 1986-06-02 AT AT86107418T patent/ATE71625T1/de not_active IP Right Cessation
- 1986-06-02 EP EP86107418A patent/EP0204285B1/en not_active Expired - Lifetime
- 1986-06-02 DE DE8686107418T patent/DE3683403D1/de not_active Expired - Fee Related
- 1986-06-03 HU HU862332A patent/HUT40798A/hu unknown
- 1986-06-03 CN CN198686104313A patent/CN86104313A/zh active Pending
- 1986-06-03 NO NO862208A patent/NO862208L/no unknown
- 1986-06-03 ES ES555653A patent/ES8800943A1/es not_active Expired
- 1986-06-04 AU AU58345/86A patent/AU593802B2/en not_active Ceased
- 1986-06-04 KR KR1019860004418A patent/KR870000332A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0204285A1 (en) | 1986-12-10 |
| FI862210A (fi) | 1986-12-05 |
| FI862210A0 (fi) | 1986-05-26 |
| CN86104313A (zh) | 1987-03-04 |
| ES8800943A1 (es) | 1987-12-01 |
| HUT40798A (en) | 1987-02-27 |
| AU5834586A (en) | 1986-12-11 |
| EP0204285B1 (en) | 1992-01-15 |
| AU593802B2 (en) | 1990-02-22 |
| ATE71625T1 (de) | 1992-02-15 |
| ES555653A0 (es) | 1987-12-01 |
| CA1257264A (en) | 1989-07-11 |
| DK250386D0 (da) | 1986-05-28 |
| NO862208D0 (no) | 1986-06-03 |
| IL78923A0 (en) | 1986-09-30 |
| GR861379B (en) | 1986-08-28 |
| DE3683403D1 (de) | 1992-02-27 |
| KR870000332A (ko) | 1987-02-17 |
| US4725601A (en) | 1988-02-16 |
| DK250386A (da) | 1986-12-05 |
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