JPH046713B2 - - Google Patents
Info
- Publication number
- JPH046713B2 JPH046713B2 JP57142733A JP14273382A JPH046713B2 JP H046713 B2 JPH046713 B2 JP H046713B2 JP 57142733 A JP57142733 A JP 57142733A JP 14273382 A JP14273382 A JP 14273382A JP H046713 B2 JPH046713 B2 JP H046713B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- imidazo
- methoxy
- hydroxy
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 cyanomethoxy Chemical group 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000006266 etherification reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 235000010233 benzoic acid Nutrition 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000101 thioether group Chemical group 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 3
- JQUKCPUPFALELS-UHFFFAOYSA-N 2-(2-methoxy-4-methylsulfinylphenyl)-3H-imidazo[4,5-c]pyridine Chemical compound COC1=CC(S(C)=O)=CC=C1C1=NC2=CC=NC=C2N1 JQUKCPUPFALELS-UHFFFAOYSA-N 0.000 claims description 2
- VIAYAQOWOLUQNX-UHFFFAOYSA-N 2-(2-methoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 VIAYAQOWOLUQNX-UHFFFAOYSA-N 0.000 claims description 2
- DNCRQPWXCICAHX-UHFFFAOYSA-N 2-[2-methoxy-4-(methylthio)phenyl]-3H-imidazo[4,5-c]pyridine Chemical compound COC1=CC(SC)=CC=C1C1=NC2=CC=NC=C2N1 DNCRQPWXCICAHX-UHFFFAOYSA-N 0.000 claims description 2
- CIXSUNSSYGNEQW-UHFFFAOYSA-N 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-methoxyphenoxy]acetonitrile Chemical compound COC1=CC(OCC#N)=CC=C1C1=NC2=NC=CC=C2N1 CIXSUNSSYGNEQW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- JPTIRCSMFNWBQW-UHFFFAOYSA-N 2-(2-methoxy-4-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 JPTIRCSMFNWBQW-UHFFFAOYSA-N 0.000 claims 1
- KUXZGRCCXVZOJT-UHFFFAOYSA-N imidazo[4,5-c]pyridine Chemical compound C1=N[CH]C2=NC=NC2=C1 KUXZGRCCXVZOJT-UHFFFAOYSA-N 0.000 claims 1
- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical group C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 25
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 19
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 19
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000005336 allyloxy group Chemical group 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RIZQKJHWYJFKAP-UHFFFAOYSA-N 2-methoxy-4-prop-2-ynoxybenzoic acid Chemical compound COC1=CC(OCC#C)=CC=C1C(O)=O RIZQKJHWYJFKAP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002440 hydroxy compounds Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000009090 positive inotropic effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005732 thioetherification reaction 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
- IDPUFCKSPSLZOI-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 IDPUFCKSPSLZOI-UHFFFAOYSA-N 0.000 description 3
- HRFYYZJGIFWLQF-UHFFFAOYSA-N 4-prop-2-ynoxybenzoic acid Chemical compound OC(=O)C1=CC=C(OCC#C)C=C1 HRFYYZJGIFWLQF-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 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
- 238000001816 cooling Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- YAVTUWLDUGMEAE-UHFFFAOYSA-N 2-(4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 YAVTUWLDUGMEAE-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- KKEKQUFCHXYNCD-UHFFFAOYSA-N 2-methoxy-4-prop-2-ynoxybenzaldehyde Chemical compound COC1=CC(OCC#C)=CC=C1C=O KKEKQUFCHXYNCD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- OJJPWYJRUUYQEV-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)-3-methoxybenzenethiol Chemical compound COC1=CC(S)=CC=C1C1=NC2=CN=CC=C2N1 OJJPWYJRUUYQEV-UHFFFAOYSA-N 0.000 description 2
- GSSBOYWRKTVVQX-UHFFFAOYSA-N 4-prop-2-ynoxybenzaldehyde Chemical compound O=CC1=CC=C(OCC#C)C=C1 GSSBOYWRKTVVQX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 description 2
- 229960004012 amifampridine Drugs 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- IIFCLXHRIYTHPV-UHFFFAOYSA-N methyl 2,4-dihydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C=C1O IIFCLXHRIYTHPV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- XMFCOYRWYYXZMY-UHFFFAOYSA-N sulmazole Chemical compound COC1=CC(S(C)=O)=CC=C1C1=NC2=NC=CC=C2N1 XMFCOYRWYYXZMY-UHFFFAOYSA-N 0.000 description 2
- 229950006153 sulmazole Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IMDUCOGJLUHBBK-UHFFFAOYSA-N (2-methoxy-4-prop-2-ynoxyphenyl)-morpholin-4-ylmethanone Chemical compound COC1=CC(OCC#C)=CC=C1C(=O)N1CCOCC1 IMDUCOGJLUHBBK-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- VKZARWJTVIJJPT-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(2-methoxy-4-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC(S(C)=O)=CC=C1C1=NC2=CN=CC=C2N1 VKZARWJTVIJJPT-WLHGVMLRSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- FNOVOVAXDCTGOR-UHFFFAOYSA-N 2,4-bis(prop-2-ynoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCC#C)C=C1OCC#C FNOVOVAXDCTGOR-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- GWBYRWHAVJKJLY-UHFFFAOYSA-N 2-(1H-imidazo[4,5-b]pyridin-2-yl)-5-prop-2-ynoxyphenol Chemical compound OC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 GWBYRWHAVJKJLY-UHFFFAOYSA-N 0.000 description 1
- DOEORTDKWHNPOY-UHFFFAOYSA-N 2-(2,4-diethoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 DOEORTDKWHNPOY-UHFFFAOYSA-N 0.000 description 1
- NIPOWUUNVUZJJG-UHFFFAOYSA-N 2-(2-ethoxy-3-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CCOC1=C(OCC#C)C=CC=C1C1=NC2=NC=CC=C2N1 NIPOWUUNVUZJJG-UHFFFAOYSA-N 0.000 description 1
- DZXCVGBRENGDPT-UHFFFAOYSA-N 2-(2-ethoxy-3-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=C(OCC#C)C=CC=C1C1=NC2=CN=CC=C2N1 DZXCVGBRENGDPT-UHFFFAOYSA-N 0.000 description 1
- OKHINBUTNSUFBX-UHFFFAOYSA-N 2-(2-ethoxy-4-methoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 OKHINBUTNSUFBX-UHFFFAOYSA-N 0.000 description 1
- IWYNXKASSYULTB-UHFFFAOYSA-N 2-(2-ethoxy-4-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(SC)=CC=C1C1=NC2=CN=CC=C2N1 IWYNXKASSYULTB-UHFFFAOYSA-N 0.000 description 1
- UYBDNBWOAQZDQB-UHFFFAOYSA-N 2-(2-ethoxy-4-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(S(C)=O)=CC=C1C1=NC2=CN=CC=C2N1 UYBDNBWOAQZDQB-UHFFFAOYSA-N 0.000 description 1
- HKPPXPCAUHDLSD-UHFFFAOYSA-N 2-(2-ethoxy-4-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CCOC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 HKPPXPCAUHDLSD-UHFFFAOYSA-N 0.000 description 1
- LXBDHAXJALGYDG-UHFFFAOYSA-N 2-(2-ethoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 LXBDHAXJALGYDG-UHFFFAOYSA-N 0.000 description 1
- GNIQQKOSRDFCKK-UHFFFAOYSA-N 2-(2-ethoxy-5-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC=C(OCC#C)C=C1C1=NC2=CN=CC=C2N1 GNIQQKOSRDFCKK-UHFFFAOYSA-N 0.000 description 1
- CELQOBSMDUMJPJ-UHFFFAOYSA-N 2-(2-ethoxy-6-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CCOC1=CC=CC(OCC#C)=C1C1=NC2=NC=CC=C2N1 CELQOBSMDUMJPJ-UHFFFAOYSA-N 0.000 description 1
- UMWTUPNZSDOOFF-UHFFFAOYSA-N 2-(2-ethoxy-6-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC=CC(OCC#C)=C1C1=NC2=CN=CC=C2N1 UMWTUPNZSDOOFF-UHFFFAOYSA-N 0.000 description 1
- JAUKCDVMIHPTKC-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC=CC=C1C1=NC2=CN=CC=C2N1 JAUKCDVMIHPTKC-UHFFFAOYSA-N 0.000 description 1
- FKQMOBXLVPUDMO-UHFFFAOYSA-N 2-(2-ethylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 FKQMOBXLVPUDMO-UHFFFAOYSA-N 0.000 description 1
- ODKZNKBXGCBULD-UHFFFAOYSA-N 2-(2-ethylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 ODKZNKBXGCBULD-UHFFFAOYSA-N 0.000 description 1
- BGEOSNSROFJZMW-UHFFFAOYSA-N 2-(2-methoxy-3-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=C(OCC#C)C=CC=C1C1=NC2=NC=CC=C2N1 BGEOSNSROFJZMW-UHFFFAOYSA-N 0.000 description 1
- BEWKCNLCBVLXQQ-UHFFFAOYSA-N 2-(2-methoxy-3-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=C(OCC#C)C=CC=C1C1=NC2=CN=CC=C2N1 BEWKCNLCBVLXQQ-UHFFFAOYSA-N 0.000 description 1
- LMAGMIYNWNPGLS-UHFFFAOYSA-N 2-(2-methoxy-4-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine;hydrochloride Chemical compound Cl.COC1=CC(SC)=CC=C1C1=NC2=CC=NC=C2N1 LMAGMIYNWNPGLS-UHFFFAOYSA-N 0.000 description 1
- JUWKYSYIWLRZMH-UHFFFAOYSA-N 2-(2-methoxy-4-phenylmethoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=C(C=2NC3=CC=CN=C3N=2)C(OC)=CC=1OCC1=CC=CC=C1 JUWKYSYIWLRZMH-UHFFFAOYSA-N 0.000 description 1
- MEUSSYUFPNGLMX-UHFFFAOYSA-N 2-(2-methoxy-4-phenylmethoxyphenyl)-3h-imidazo[4,5-c]pyridine;hydrochloride Chemical compound Cl.C=1C=C(C=2NC3=CC=NC=C3N=2)C(OC)=CC=1OCC1=CC=CC=C1 MEUSSYUFPNGLMX-UHFFFAOYSA-N 0.000 description 1
- LGXMLPOPAXXZJQ-UHFFFAOYSA-N 2-(2-methoxy-4-prop-2-ynylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(SCC#C)=CC=C1C1=NC2=CC=NC=C2N1 LGXMLPOPAXXZJQ-UHFFFAOYSA-N 0.000 description 1
- KPQRAWSIFOTFCF-UHFFFAOYSA-N 2-(2-methoxy-4-prop-2-ynylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(S(=O)CC#C)=CC=C1C1=NC2=CN=CC=C2N1 KPQRAWSIFOTFCF-UHFFFAOYSA-N 0.000 description 1
- NSGAPPWZJPYAKL-UHFFFAOYSA-N 2-(2-methoxy-4-propan-2-yloxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(OC(C)C)=CC=C1C1=NC2=CN=CC=C2N1 NSGAPPWZJPYAKL-UHFFFAOYSA-N 0.000 description 1
- XFSXOBPFLRQUSE-UHFFFAOYSA-N 2-(2-methoxy-5-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC=C(SC)C=C1C1=NC2=CN=CC=C2N1 XFSXOBPFLRQUSE-UHFFFAOYSA-N 0.000 description 1
- YWRJSBICVQXIJW-UHFFFAOYSA-N 2-(2-methoxy-6-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=CC(OCC#C)=C1C1=NC2=NC=CC=C2N1 YWRJSBICVQXIJW-UHFFFAOYSA-N 0.000 description 1
- OWWDWGFTRMACQN-UHFFFAOYSA-N 2-(2-methoxy-6-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC=CC(OCC#C)=C1C1=NC2=CN=CC=C2N1 OWWDWGFTRMACQN-UHFFFAOYSA-N 0.000 description 1
- FTDNAOQEXRNSTD-UHFFFAOYSA-N 2-(2-methylsulfanyl-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 FTDNAOQEXRNSTD-UHFFFAOYSA-N 0.000 description 1
- IBBGDDVUVGEJEN-UHFFFAOYSA-N 2-(2-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 IBBGDDVUVGEJEN-UHFFFAOYSA-N 0.000 description 1
- AITAGTBPAGVVRW-UHFFFAOYSA-N 2-(2-methylsulfinyl-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CS(=O)C1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 AITAGTBPAGVVRW-UHFFFAOYSA-N 0.000 description 1
- ISJGBNFGJXBOCS-UHFFFAOYSA-N 2-(2-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 ISJGBNFGJXBOCS-UHFFFAOYSA-N 0.000 description 1
- VBJIETXXOKUXGN-UHFFFAOYSA-N 2-(2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC=CC=C1C1=NC2=CN=CC=C2N1 VBJIETXXOKUXGN-UHFFFAOYSA-N 0.000 description 1
- VLRQZCSLDSAARR-UHFFFAOYSA-N 2-(2-prop-2-ynylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 VLRQZCSLDSAARR-UHFFFAOYSA-N 0.000 description 1
- FAABCXDGLZVRKF-UHFFFAOYSA-N 2-(2-prop-2-ynylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 FAABCXDGLZVRKF-UHFFFAOYSA-N 0.000 description 1
- RIFWPHMSJMJTNL-UHFFFAOYSA-N 2-(2-propan-2-yloxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CC(C)OC1=CC=CC=C1C1=NC2=CN=CC=C2N1 RIFWPHMSJMJTNL-UHFFFAOYSA-N 0.000 description 1
- YEJIUYYZBVHPME-UHFFFAOYSA-N 2-(2-propoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCOC1=CC=CC=C1C1=NC2=CN=CC=C2N1 YEJIUYYZBVHPME-UHFFFAOYSA-N 0.000 description 1
- XTHIEXVYVFBPCW-UHFFFAOYSA-N 2-(2-propylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 XTHIEXVYVFBPCW-UHFFFAOYSA-N 0.000 description 1
- QUXHHFWYVBIRLA-UHFFFAOYSA-N 2-(2-propylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 QUXHHFWYVBIRLA-UHFFFAOYSA-N 0.000 description 1
- DIFDEPSLODWUPV-UHFFFAOYSA-N 2-(3,5-diethoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=C(OCC#C)C(OCC)=CC(C=2NC3=CC=NC=C3N=2)=C1 DIFDEPSLODWUPV-UHFFFAOYSA-N 0.000 description 1
- TWDKZHLEECDQJV-UHFFFAOYSA-N 2-(3,5-dimethoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=C(OCC#C)C(OC)=CC(C=2NC3=CC=NC=C3N=2)=C1 TWDKZHLEECDQJV-UHFFFAOYSA-N 0.000 description 1
- WMBSEOZUYREIIE-UHFFFAOYSA-N 2-(3-ethoxy-2-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CCOC1=CC=CC(C=2NC3=CC=CN=C3N=2)=C1OCC#C WMBSEOZUYREIIE-UHFFFAOYSA-N 0.000 description 1
- CYKONNBOIQVQKH-UHFFFAOYSA-N 2-(3-ethoxy-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1OCC#C CYKONNBOIQVQKH-UHFFFAOYSA-N 0.000 description 1
- HHSSNKOKHSPJFO-UHFFFAOYSA-N 2-(3-ethoxy-4-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(OCC#C)C(OCC)=CC(C=2NC3=CC=CN=C3N=2)=C1 HHSSNKOKHSPJFO-UHFFFAOYSA-N 0.000 description 1
- MTVAZYGBWDRWDJ-UHFFFAOYSA-N 2-(3-ethoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=C(OCC#C)C(OCC)=CC(C=2NC3=CC=NC=C3N=2)=C1 MTVAZYGBWDRWDJ-UHFFFAOYSA-N 0.000 description 1
- XHIYBYQZYYYAAR-UHFFFAOYSA-N 2-(3-ethoxy-5-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CCOC1=CC(OCC#C)=CC(C=2NC3=CC=CN=C3N=2)=C1 XHIYBYQZYYYAAR-UHFFFAOYSA-N 0.000 description 1
- ZSJJWSGUVNTZTC-UHFFFAOYSA-N 2-(3-ethoxy-5-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC(OCC#C)=CC(C=2NC3=CC=NC=C3N=2)=C1 ZSJJWSGUVNTZTC-UHFFFAOYSA-N 0.000 description 1
- KXXNIFAZHJXCLZ-UHFFFAOYSA-N 2-(3-ethoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 KXXNIFAZHJXCLZ-UHFFFAOYSA-N 0.000 description 1
- ANKWHUFZWXXEPP-UHFFFAOYSA-N 2-(3-ethylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 ANKWHUFZWXXEPP-UHFFFAOYSA-N 0.000 description 1
- XPLBTJQUTGEVCW-UHFFFAOYSA-N 2-(3-ethylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 XPLBTJQUTGEVCW-UHFFFAOYSA-N 0.000 description 1
- ILTRVXJPGZNKGR-UHFFFAOYSA-N 2-(3-methoxy-2-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=CC(C=2NC3=CC=CN=C3N=2)=C1OCC#C ILTRVXJPGZNKGR-UHFFFAOYSA-N 0.000 description 1
- DQMCNYTUTVGQKJ-UHFFFAOYSA-N 2-(3-methoxy-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1OCC#C DQMCNYTUTVGQKJ-UHFFFAOYSA-N 0.000 description 1
- LZGGLOQKKMLHPY-UHFFFAOYSA-N 2-(3-methoxy-4-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=C(OCC#C)C(OC)=CC(C=2NC3=CC=NC=C3N=2)=C1 LZGGLOQKKMLHPY-UHFFFAOYSA-N 0.000 description 1
- JDOGPLAMPXRDQZ-UHFFFAOYSA-N 2-(3-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 JDOGPLAMPXRDQZ-UHFFFAOYSA-N 0.000 description 1
- PRLKLCUTPFURKE-UHFFFAOYSA-N 2-(3-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 PRLKLCUTPFURKE-UHFFFAOYSA-N 0.000 description 1
- GIGDOZAHULXSHD-UHFFFAOYSA-N 2-(3-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 GIGDOZAHULXSHD-UHFFFAOYSA-N 0.000 description 1
- PMCFUIURXWGNPX-UHFFFAOYSA-N 2-(3-prop-2-ynylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 PMCFUIURXWGNPX-UHFFFAOYSA-N 0.000 description 1
- SZQAYDVMICIURW-UHFFFAOYSA-N 2-(3-prop-2-ynylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 SZQAYDVMICIURW-UHFFFAOYSA-N 0.000 description 1
- ODSJNWBMQKFVEL-UHFFFAOYSA-N 2-(3-propan-2-yloxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CC(C)OC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 ODSJNWBMQKFVEL-UHFFFAOYSA-N 0.000 description 1
- YKNZUIICAUMCGR-UHFFFAOYSA-N 2-(3-propoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 YKNZUIICAUMCGR-UHFFFAOYSA-N 0.000 description 1
- LNMMLZPITCILRE-UHFFFAOYSA-N 2-(3-propylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 LNMMLZPITCILRE-UHFFFAOYSA-N 0.000 description 1
- FXWKOXSJHNQQEJ-UHFFFAOYSA-N 2-(3-propylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CCCS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 FXWKOXSJHNQQEJ-UHFFFAOYSA-N 0.000 description 1
- FVQIIKKZQUARCH-UHFFFAOYSA-N 2-(3H-imidazo[4,5-c]pyridin-2-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 FVQIIKKZQUARCH-UHFFFAOYSA-N 0.000 description 1
- YNQQWQKNGHLMRX-UHFFFAOYSA-N 2-(3H-imidazo[4,5-c]pyridin-2-yl)-5-methylsulfanylphenol Chemical compound OC1=C(C=CC(=C1)SC)C=1NC2=C(C=NC=C2)N1 YNQQWQKNGHLMRX-UHFFFAOYSA-N 0.000 description 1
- BBSNFJUVJLSPIA-UHFFFAOYSA-N 2-(3H-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxybenzenethiol Chemical compound SC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 BBSNFJUVJLSPIA-UHFFFAOYSA-N 0.000 description 1
- AZAQRILGUMHDCT-UHFFFAOYSA-N 2-(3H-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxyphenol Chemical compound OC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 AZAQRILGUMHDCT-UHFFFAOYSA-N 0.000 description 1
- FIKHVURBSANKOA-UHFFFAOYSA-N 2-(3H-imidazo[4,5-c]pyridin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CN=CC=C2N1 FIKHVURBSANKOA-UHFFFAOYSA-N 0.000 description 1
- GZEVOMCZWKRMQY-UHFFFAOYSA-N 2-(4-ethoxy-2-methoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 GZEVOMCZWKRMQY-UHFFFAOYSA-N 0.000 description 1
- ULPJYHRVRYSVKX-UHFFFAOYSA-N 2-(4-ethoxy-2-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC(OCC)=CC=C1C1=NC2=CC=NC=C2N1 ULPJYHRVRYSVKX-UHFFFAOYSA-N 0.000 description 1
- ADPAHRMUWQGWEJ-UHFFFAOYSA-N 2-(4-ethoxy-2-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CS(=O)C1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 ADPAHRMUWQGWEJ-UHFFFAOYSA-N 0.000 description 1
- NJYJQKGIPCLRDJ-UHFFFAOYSA-N 2-(4-ethoxy-2-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C#CCOC1=CC(OCC)=CC=C1C1=NC2=NC=CC=C2N1 NJYJQKGIPCLRDJ-UHFFFAOYSA-N 0.000 description 1
- LBCHZMRLZNOVCO-UHFFFAOYSA-N 2-(4-ethoxy-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 LBCHZMRLZNOVCO-UHFFFAOYSA-N 0.000 description 1
- CYJREPABRIILLA-UHFFFAOYSA-N 2-(4-ethoxy-3-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(OCC#C)C(OCC)=CC=C1C1=NC2=NC=CC=C2N1 CYJREPABRIILLA-UHFFFAOYSA-N 0.000 description 1
- JQQRSNWNXFJVFJ-UHFFFAOYSA-N 2-(4-ethoxy-3-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=C(OCC#C)C(OCC)=CC=C1C1=NC2=CN=CC=C2N1 JQQRSNWNXFJVFJ-UHFFFAOYSA-N 0.000 description 1
- WDCMIJCRNABEBO-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 WDCMIJCRNABEBO-UHFFFAOYSA-N 0.000 description 1
- PDTNLSUKGWQTKO-UHFFFAOYSA-N 2-(4-ethylsulfanyl-2-methoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(SCC)=CC=C1C1=NC2=CN=CC=C2N1 PDTNLSUKGWQTKO-UHFFFAOYSA-N 0.000 description 1
- NSBAVSYYNUNZGC-UHFFFAOYSA-N 2-(4-ethylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(SCC)=CC=C1C1=NC2=CN=CC=C2N1 NSBAVSYYNUNZGC-UHFFFAOYSA-N 0.000 description 1
- NCXLEBCJNGCVFS-UHFFFAOYSA-N 2-(4-ethylsulfinyl-2-methoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC(S(=O)CC)=CC=C1C1=NC2=CN=CC=C2N1 NCXLEBCJNGCVFS-UHFFFAOYSA-N 0.000 description 1
- UXJXTXLAIIVQEQ-UHFFFAOYSA-N 2-(4-ethylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(S(=O)CC)=CC=C1C1=NC2=CN=CC=C2N1 UXJXTXLAIIVQEQ-UHFFFAOYSA-N 0.000 description 1
- AEUIABKBLSYCEQ-UHFFFAOYSA-N 2-(4-methoxy-2-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 AEUIABKBLSYCEQ-UHFFFAOYSA-N 0.000 description 1
- XCCSHEWQVWCIIC-UHFFFAOYSA-N 2-(4-methoxy-2-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound CS(=O)C1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 XCCSHEWQVWCIIC-UHFFFAOYSA-N 0.000 description 1
- MFFOWWYEXPSHGK-UHFFFAOYSA-N 2-(4-methoxy-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 MFFOWWYEXPSHGK-UHFFFAOYSA-N 0.000 description 1
- XWMGYEHRJDOGOS-UHFFFAOYSA-N 2-(4-methoxy-3-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(OCC#C)C(OC)=CC=C1C1=NC2=NC=CC=C2N1 XWMGYEHRJDOGOS-UHFFFAOYSA-N 0.000 description 1
- MJTBTWNEZNQKPV-UHFFFAOYSA-N 2-(4-methoxy-3-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=C(OCC#C)C(OC)=CC=C1C1=NC2=CN=CC=C2N1 MJTBTWNEZNQKPV-UHFFFAOYSA-N 0.000 description 1
- SDBKNJXXGNHUJI-UHFFFAOYSA-N 2-(4-methylsulfanyl-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC(SC)=CC=C1C1=NC2=CN=CC=C2N1 SDBKNJXXGNHUJI-UHFFFAOYSA-N 0.000 description 1
- ZAFBUZHSYWIITP-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(SC)=CC=C1C1=NC2=CN=CC=C2N1 ZAFBUZHSYWIITP-UHFFFAOYSA-N 0.000 description 1
- BELSQPPWUJTTSP-UHFFFAOYSA-N 2-(4-methylsulfinyl-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C#CCOC1=CC(S(=O)C)=CC=C1C1=NC2=CN=CC=C2N1 BELSQPPWUJTTSP-UHFFFAOYSA-N 0.000 description 1
- OUXOATBBSNUXHW-UHFFFAOYSA-N 2-(4-methylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(S(=O)C)=CC=C1C1=NC2=CN=CC=C2N1 OUXOATBBSNUXHW-UHFFFAOYSA-N 0.000 description 1
- FUGSUGAVRLLRGX-UHFFFAOYSA-N 2-(4-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 FUGSUGAVRLLRGX-UHFFFAOYSA-N 0.000 description 1
- OYXNCDBSZRQAOF-UHFFFAOYSA-N 2-(4-prop-2-ynylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(S(CC#C)=O)=CC=C1C1=NC2=CN=CC=C2N1 OYXNCDBSZRQAOF-UHFFFAOYSA-N 0.000 description 1
- ZOQDSBZOHCJAHI-UHFFFAOYSA-N 2-(4-propan-2-yloxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(OC(C)C)=CC=C1C1=NC2=CN=CC=C2N1 ZOQDSBZOHCJAHI-UHFFFAOYSA-N 0.000 description 1
- WHUPPEJRGMNOMR-UHFFFAOYSA-N 2-(4-propoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(OCCC)=CC=C1C1=NC2=CN=CC=C2N1 WHUPPEJRGMNOMR-UHFFFAOYSA-N 0.000 description 1
- IWDNDYYGLKTBQV-UHFFFAOYSA-N 2-(4-propylsulfanylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(SCCC)=CC=C1C1=NC2=CN=CC=C2N1 IWDNDYYGLKTBQV-UHFFFAOYSA-N 0.000 description 1
- OLFFGVSMDBIEKY-UHFFFAOYSA-N 2-(4-propylsulfinylphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound C1=CC(S(=O)CCC)=CC=C1C1=NC2=CN=CC=C2N1 OLFFGVSMDBIEKY-UHFFFAOYSA-N 0.000 description 1
- OFYFZSRBMWHILP-UHFFFAOYSA-N 2-(5-methoxy-2-prop-2-ynoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=C(OCC#C)C(C=2NC3=CC=CN=C3N=2)=C1 OFYFZSRBMWHILP-UHFFFAOYSA-N 0.000 description 1
- JBRSFEQPNFEBBL-UHFFFAOYSA-N 2-(5-methoxy-2-prop-2-ynoxyphenyl)-3h-imidazo[4,5-c]pyridine Chemical compound COC1=CC=C(OCC#C)C(C=2NC3=CC=NC=C3N=2)=C1 JBRSFEQPNFEBBL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YUMWBJNBHRBGIQ-UHFFFAOYSA-N 2-[2,4-bis(methylsulfanyl)phenyl]-3h-imidazo[4,5-c]pyridine Chemical compound CSC1=CC(SC)=CC=C1C1=NC2=CN=CC=C2N1 YUMWBJNBHRBGIQ-UHFFFAOYSA-N 0.000 description 1
- MUVQEFITUGQBLL-UHFFFAOYSA-N 2-[2,4-bis(prop-2-ynoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C#CCOC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 MUVQEFITUGQBLL-UHFFFAOYSA-N 0.000 description 1
- DRNNZGVDWTXUAJ-UHFFFAOYSA-N 2-[2,4-di(propan-2-yloxy)phenyl]-3h-imidazo[4,5-c]pyridine Chemical compound CC(C)OC1=CC(OC(C)C)=CC=C1C1=NC2=CN=CC=C2N1 DRNNZGVDWTXUAJ-UHFFFAOYSA-N 0.000 description 1
- HEPGGIHOGNDSOM-UHFFFAOYSA-N 2-[2-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC=CC=C1C1=NC2=NC=CC=C2N1 HEPGGIHOGNDSOM-UHFFFAOYSA-N 0.000 description 1
- DKZHUCOCXJZAHQ-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-methoxyphenoxy]acetonitrile Chemical compound N#CCOC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 DKZHUCOCXJZAHQ-UHFFFAOYSA-N 0.000 description 1
- JYLDMRDGIYSZMF-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-methoxyphenoxy]ethanol Chemical compound OCCOC1=CC(OC)=CC=C1C1=NC2=CN=CC=C2N1 JYLDMRDGIYSZMF-UHFFFAOYSA-N 0.000 description 1
- ZJLPQVWJAFECRL-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-methylsulfanylphenoxy]acetonitrile Chemical compound N#CCOC1=CC(SC)=CC=C1C1=NC2=CC=NC=C2N1 ZJLPQVWJAFECRL-UHFFFAOYSA-N 0.000 description 1
- YGCPMWJPHUUKTL-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-methylsulfinylphenoxy]acetonitrile Chemical compound N#CCOC1=CC(S(=O)C)=CC=C1C1=NC2=CN=CC=C2N1 YGCPMWJPHUUKTL-UHFFFAOYSA-N 0.000 description 1
- BTDCZCVTKOHVPY-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]acetonitrile Chemical compound N#CCOC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 BTDCZCVTKOHVPY-UHFFFAOYSA-N 0.000 description 1
- PJHAXNICDKUQLX-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]ethanol Chemical compound OCCOC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 PJHAXNICDKUQLX-UHFFFAOYSA-N 0.000 description 1
- UVENWCVPRFLCBF-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC=CC=C1C1=NC2=CN=CC=C2N1 UVENWCVPRFLCBF-UHFFFAOYSA-N 0.000 description 1
- REJMXICFRKKECH-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound OCCOC1=CC=CC=C1C1=NC2=CN=CC=C2N1 REJMXICFRKKECH-UHFFFAOYSA-N 0.000 description 1
- YIBZGTPGJWTMRM-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetonitrile Chemical compound N#CCSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 YIBZGTPGJWTMRM-UHFFFAOYSA-N 0.000 description 1
- ARPMHROUKTUTGR-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylethanol Chemical compound OCCSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 ARPMHROUKTUTGR-UHFFFAOYSA-N 0.000 description 1
- KBCCVZBCXOFTRL-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetonitrile Chemical compound N#CCS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 KBCCVZBCXOFTRL-UHFFFAOYSA-N 0.000 description 1
- KFXGCLIETOSZBQ-UHFFFAOYSA-N 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylethanol Chemical compound OCCS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 KFXGCLIETOSZBQ-UHFFFAOYSA-N 0.000 description 1
- GLYRBSKNVKHDAP-UHFFFAOYSA-N 2-[3-(2-hydroxyethoxy)-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound OCCOC1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 GLYRBSKNVKHDAP-UHFFFAOYSA-N 0.000 description 1
- ICQATDWYSMZPJM-UHFFFAOYSA-N 2-[3-(2-hydroxyethoxy)-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound OCCOC1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 ICQATDWYSMZPJM-UHFFFAOYSA-N 0.000 description 1
- NRAWNWSZXUGBHI-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 NRAWNWSZXUGBHI-UHFFFAOYSA-N 0.000 description 1
- CUVGUEFTVLADGI-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound OCCOC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 CUVGUEFTVLADGI-UHFFFAOYSA-N 0.000 description 1
- ZAKIOMKDRXYPMM-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetonitrile Chemical compound N#CCSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 ZAKIOMKDRXYPMM-UHFFFAOYSA-N 0.000 description 1
- LONXAWJCLJOUAJ-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylethanol Chemical compound OCCSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 LONXAWJCLJOUAJ-UHFFFAOYSA-N 0.000 description 1
- HJUHTHSDMULGFA-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetonitrile Chemical compound N#CCS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 HJUHTHSDMULGFA-UHFFFAOYSA-N 0.000 description 1
- QEGBYYMAUFCBAJ-UHFFFAOYSA-N 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylethanol Chemical compound OCCS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 QEGBYYMAUFCBAJ-UHFFFAOYSA-N 0.000 description 1
- JBMVFAGRWGDLBK-UHFFFAOYSA-N 2-[3-(cyanomethoxy)-4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC(OCC#N)=CC=C1C1=NC2=NC=CC=C2N1 JBMVFAGRWGDLBK-UHFFFAOYSA-N 0.000 description 1
- PKSWLSKPJPAINW-UHFFFAOYSA-N 2-[3-ethoxy-4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetonitrile Chemical compound CCOC1=CC(OCC#N)=CC=C1C1=NC2=NC=CC=C2N1 PKSWLSKPJPAINW-UHFFFAOYSA-N 0.000 description 1
- NCLKBMSJHSSOBC-UHFFFAOYSA-N 2-[3-ethoxy-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound CCOC1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 NCLKBMSJHSSOBC-UHFFFAOYSA-N 0.000 description 1
- YTFJZJQLQWARAQ-UHFFFAOYSA-N 2-[3-ethoxy-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound CCOC1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 YTFJZJQLQWARAQ-UHFFFAOYSA-N 0.000 description 1
- PJNPGBSEJIJTBH-UHFFFAOYSA-N 2-[3-hydroxy-4-(1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetonitrile Chemical compound OC1=CC(OCC#N)=CC=C1C1=NC2=NC=CC=C2N1 PJNPGBSEJIJTBH-UHFFFAOYSA-N 0.000 description 1
- NDNUCSFRBXPPRA-UHFFFAOYSA-N 2-[3-hydroxy-4-(3H-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound OC1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 NDNUCSFRBXPPRA-UHFFFAOYSA-N 0.000 description 1
- NUCQRMQTRFGASE-UHFFFAOYSA-N 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetonitrile Chemical compound C1=CC(OCC#N)=CC=C1C1=NC2=NC=CC=C2N1 NUCQRMQTRFGASE-UHFFFAOYSA-N 0.000 description 1
- IBYUWIROEMJTRA-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-1-methoxycyclohexa-2,4-dien-1-yl]oxyethanol Chemical compound C1=CC(OC)(OCCO)CC=C1C1=NC2=CN=CC=C2N1 IBYUWIROEMJTRA-UHFFFAOYSA-N 0.000 description 1
- MWAQOHCHYZPGEO-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenoxy]acetonitrile Chemical compound COC1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 MWAQOHCHYZPGEO-UHFFFAOYSA-N 0.000 description 1
- XJZBVGIUSURYDW-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfanylacetonitrile Chemical compound COC1=CC(SCC#N)=CC=C1C1=NC2=CN=CC=C2N1 XJZBVGIUSURYDW-UHFFFAOYSA-N 0.000 description 1
- HXUIQXSUYABRBR-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfinylacetic acid Chemical compound COC1=CC(S(=O)CC(O)=O)=CC=C1C1=NC2=CN=CC=C2N1 HXUIQXSUYABRBR-UHFFFAOYSA-N 0.000 description 1
- AUYIUWZGXFCICK-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfinylacetonitrile Chemical compound COC1=CC(S(=O)CC#N)=CC=C1C1=NC2=CN=CC=C2N1 AUYIUWZGXFCICK-UHFFFAOYSA-N 0.000 description 1
- OTTYYIFXYGDZAK-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methylsulfanylphenoxy]acetonitrile Chemical compound CSC1=CC(OCC#N)=CC=C1C1=NC2=CC=NC=C2N1 OTTYYIFXYGDZAK-UHFFFAOYSA-N 0.000 description 1
- OJMNGTDCUZYFTD-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methylsulfinylphenoxy]acetonitrile Chemical compound CS(=O)C1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 OJMNGTDCUZYFTD-UHFFFAOYSA-N 0.000 description 1
- IPVDVQPRTVIWSO-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-prop-2-ynoxyphenoxy]ethanol Chemical compound C#CCOC1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 IPVDVQPRTVIWSO-UHFFFAOYSA-N 0.000 description 1
- JRBSVMWRKWWKGX-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound C1=CC(OCC#N)=CC=C1C1=NC2=CN=CC=C2N1 JRBSVMWRKWWKGX-UHFFFAOYSA-N 0.000 description 1
- XFLCYLNXZWRJEB-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 XFLCYLNXZWRJEB-UHFFFAOYSA-N 0.000 description 1
- VHWLYPUTSFCUIS-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetonitrile Chemical compound C1=CC(SCC#N)=CC=C1C1=NC2=CN=CC=C2N1 VHWLYPUTSFCUIS-UHFFFAOYSA-N 0.000 description 1
- YDRRJWUFGAHWIY-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylethanol Chemical compound C1=CC(SCCO)=CC=C1C1=NC2=CN=CC=C2N1 YDRRJWUFGAHWIY-UHFFFAOYSA-N 0.000 description 1
- BZJZLEDHCKSGFN-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetonitrile Chemical compound C1=CC(S(CC#N)=O)=CC=C1C1=NC2=CN=CC=C2N1 BZJZLEDHCKSGFN-UHFFFAOYSA-N 0.000 description 1
- WAXGWPFRNXMHHB-UHFFFAOYSA-N 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylethanol Chemical compound C1=CC(S(=O)CCO)=CC=C1C1=NC2=CN=CC=C2N1 WAXGWPFRNXMHHB-UHFFFAOYSA-N 0.000 description 1
- LOCQDPWHCKNFCS-UHFFFAOYSA-N 2-[5-(2-hydroxyethoxy)-2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 LOCQDPWHCKNFCS-UHFFFAOYSA-N 0.000 description 1
- PHLOAHRMRPPTRS-UHFFFAOYSA-N 2-[5-ethoxy-2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 PHLOAHRMRPPTRS-UHFFFAOYSA-N 0.000 description 1
- CYEZFTBMYFNYOS-UHFFFAOYSA-N 2-[5-ethoxy-2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]ethanol Chemical compound OCCOC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 CYEZFTBMYFNYOS-UHFFFAOYSA-N 0.000 description 1
- VOMXXUNJXLKYOR-UHFFFAOYSA-N 2-[5-hydroxy-2-(3H-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetonitrile Chemical compound N#CCOC1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 VOMXXUNJXLKYOR-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UZENLRYJSRVUHY-UHFFFAOYSA-N 2-methoxy-4-prop-2-ynoxybenzonitrile Chemical compound COC1=CC(OCC#C)=CC=C1C#N UZENLRYJSRVUHY-UHFFFAOYSA-N 0.000 description 1
- WASUVLQNHLOOMB-UHFFFAOYSA-N 2-methoxy-5-prop-2-ynoxybenzoic acid Chemical compound COC1=CC=C(OCC#C)C=C1C(O)=O WASUVLQNHLOOMB-UHFFFAOYSA-N 0.000 description 1
- VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- PEERMPFPCWSJLC-UHFFFAOYSA-N 2-prop-2-ynoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OCC#C PEERMPFPCWSJLC-UHFFFAOYSA-N 0.000 description 1
- GWSHQLNZKYWYGT-UHFFFAOYSA-N 2-prop-2-ynoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC#C GWSHQLNZKYWYGT-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- TXCCUMZVBIKPIX-UHFFFAOYSA-N 3,5-dimethoxy-4-prop-2-ynoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OCC#C TXCCUMZVBIKPIX-UHFFFAOYSA-N 0.000 description 1
- DRDCXXRMOLNYOW-UHFFFAOYSA-N 3-(2-hydroxyethoxy)-4-(3H-imidazo[4,5-c]pyridin-2-yl)phenol Chemical compound OCCOC1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 DRDCXXRMOLNYOW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- RWMIJZWYUOCKAS-UHFFFAOYSA-N 3-ethoxy-4-(3H-imidazo[4,5-c]pyridin-2-yl)phenol Chemical compound CCOC1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 RWMIJZWYUOCKAS-UHFFFAOYSA-N 0.000 description 1
- JQBULVBEPSHSEW-UHFFFAOYSA-N 3-methoxy-4-prop-2-ynoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1OCC#C JQBULVBEPSHSEW-UHFFFAOYSA-N 0.000 description 1
- CYAQTWGCPCRKJT-UHFFFAOYSA-N 3-prop-2-ynoxybenzaldehyde Chemical compound O=CC1=CC=CC(OCC#C)=C1 CYAQTWGCPCRKJT-UHFFFAOYSA-N 0.000 description 1
- QVFUOVBWGXPWRG-UHFFFAOYSA-N 4-(1H-imidazo[4,5-b]pyridin-2-yl)-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C1=NC2=NC=CC=C2N1 QVFUOVBWGXPWRG-UHFFFAOYSA-N 0.000 description 1
- MQXOMPMIVZXSOY-UHFFFAOYSA-N 4-(1H-imidazo[4,5-b]pyridin-2-yl)-3-prop-2-ynoxyphenol Chemical compound C#CCOC1=CC(O)=CC=C1C1=NC2=NC=CC=C2N1 MQXOMPMIVZXSOY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XFZGJBWXUOWESH-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)-3-methylsulfanylphenol Chemical compound OC1=CC(=C(C=C1)C=1NC2=C(C=NC=C2)N1)SC XFZGJBWXUOWESH-UHFFFAOYSA-N 0.000 description 1
- SQCXUNLRJXTDEC-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)-3-methylsulfinylphenol Chemical compound CS(=O)C1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 SQCXUNLRJXTDEC-UHFFFAOYSA-N 0.000 description 1
- BRUNRWBIWYARAN-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)-3-prop-2-ynoxyphenol Chemical compound C#CCOC1=CC(O)=CC=C1C1=NC2=CN=CC=C2N1 BRUNRWBIWYARAN-UHFFFAOYSA-N 0.000 description 1
- OBHCMWVKESWUNF-UHFFFAOYSA-N 4-(3H-imidazo[4,5-c]pyridin-2-yl)benzenethiol Chemical compound C1=CC(S)=CC=C1C1=NC2=CN=CC=C2N1 OBHCMWVKESWUNF-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GWYPJBKNXSRAPX-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzoic acid Chemical compound COC1=CC(O)=CC=C1C(O)=O GWYPJBKNXSRAPX-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- CBCYTDXUFIOOFH-UHFFFAOYSA-N 5-(1h-imidazo[4,5-b]pyridin-2-yl)-2-prop-2-ynoxyphenol Chemical compound C1=C(OCC#C)C(O)=CC(C=2NC3=CC=CN=C3N=2)=C1 CBCYTDXUFIOOFH-UHFFFAOYSA-N 0.000 description 1
- CQVUSRQUUJKWKK-UHFFFAOYSA-N 5-(2-hydroxyethoxy)-2-(3H-imidazo[4,5-c]pyridin-2-yl)phenol Chemical compound OC1=CC(OCCO)=CC=C1C1=NC2=CN=CC=C2N1 CQVUSRQUUJKWKK-UHFFFAOYSA-N 0.000 description 1
- VXNZVVQVKDGUMF-UHFFFAOYSA-N 5-ethoxy-2-(3H-imidazo[4,5-c]pyridin-2-yl)phenol Chemical compound OC1=CC(OCC)=CC=C1C1=NC2=CN=CC=C2N1 VXNZVVQVKDGUMF-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- VCHBUGKRGMKOSM-UHFFFAOYSA-N C1=CC(OC#C)=CC=C1C1=NC2=CC=NC=C2N1 Chemical compound C1=CC(OC#C)=CC=C1C1=NC2=CC=NC=C2N1 VCHBUGKRGMKOSM-UHFFFAOYSA-N 0.000 description 1
- MDQQVKJBNKASLW-UHFFFAOYSA-N C1=CC(OC#C)=CC=C1C1=NC2=NC=CC=C2N1 Chemical compound C1=CC(OC#C)=CC=C1C1=NC2=NC=CC=C2N1 MDQQVKJBNKASLW-UHFFFAOYSA-N 0.000 description 1
- SRODEWHQXMKMSD-UHFFFAOYSA-M COC1=CC(OCC#C)=CC=C1C(N1CCOCC1)=[S+]C.[I-] Chemical compound COC1=CC(OCC#C)=CC=C1C(N1CCOCC1)=[S+]C.[I-] SRODEWHQXMKMSD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-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
- 108010010803 Gelatin Proteins 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000005109 alkynylthio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical class C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- ZDWAFUJLPGPICB-UHFFFAOYSA-N butyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCCCC)=CC=C1C1=NC2=CN=CC=C2N1 ZDWAFUJLPGPICB-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 229940082657 digitalis glycosides Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- DUEXGSFGTUHHQY-UHFFFAOYSA-N ethyl 2-[2-(1h-imidazo[4,5-b]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 DUEXGSFGTUHHQY-UHFFFAOYSA-N 0.000 description 1
- XMZWCPNHVQLDRP-UHFFFAOYSA-N ethyl 2-[2-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C1=NC2=NC=CC=C2N1 XMZWCPNHVQLDRP-UHFFFAOYSA-N 0.000 description 1
- GKRBTXQNQRJTNF-UHFFFAOYSA-N ethyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]acetate Chemical compound CCOC(=O)COC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 GKRBTXQNQRJTNF-UHFFFAOYSA-N 0.000 description 1
- NUYMSSKQVLGZPN-UHFFFAOYSA-N ethyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C1=NC2=CN=CC=C2N1 NUYMSSKQVLGZPN-UHFFFAOYSA-N 0.000 description 1
- FKFKVYJXFVHQES-UHFFFAOYSA-N ethyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 FKFKVYJXFVHQES-UHFFFAOYSA-N 0.000 description 1
- RSAVHCULFNDCPM-UHFFFAOYSA-N ethyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound CCOC(=O)CS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 RSAVHCULFNDCPM-UHFFFAOYSA-N 0.000 description 1
- YIILZLVKGOGKNI-UHFFFAOYSA-N ethyl 2-[3-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(C=2NC3=CC=CN=C3N=2)=C1 YIILZLVKGOGKNI-UHFFFAOYSA-N 0.000 description 1
- YYJLQBNLXBDSRC-UHFFFAOYSA-N ethyl 2-[3-(2-ethoxy-2-oxoethoxy)-4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 YYJLQBNLXBDSRC-UHFFFAOYSA-N 0.000 description 1
- NPMMRNCMUPHJOL-UHFFFAOYSA-N ethyl 2-[3-(2-ethoxy-2-oxoethoxy)-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 NPMMRNCMUPHJOL-UHFFFAOYSA-N 0.000 description 1
- ADOVFQRRIPLIDD-UHFFFAOYSA-N ethyl 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 ADOVFQRRIPLIDD-UHFFFAOYSA-N 0.000 description 1
- ZQQBHKNIIMMLBH-UHFFFAOYSA-N ethyl 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 ZQQBHKNIIMMLBH-UHFFFAOYSA-N 0.000 description 1
- UAGRFVUEGFLHPS-UHFFFAOYSA-N ethyl 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound CCOC(=O)CS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 UAGRFVUEGFLHPS-UHFFFAOYSA-N 0.000 description 1
- VIMMWBMMXFRODY-UHFFFAOYSA-N ethyl 2-[3-ethoxy-4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 VIMMWBMMXFRODY-UHFFFAOYSA-N 0.000 description 1
- IUNSTDUOIJCCMH-UHFFFAOYSA-N ethyl 2-[3-ethoxy-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 IUNSTDUOIJCCMH-UHFFFAOYSA-N 0.000 description 1
- LZRJINUWFGAXAD-UHFFFAOYSA-N ethyl 2-[3-hydroxy-4-(1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound OC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 LZRJINUWFGAXAD-UHFFFAOYSA-N 0.000 description 1
- JSRSBSWAHZYEMV-UHFFFAOYSA-N ethyl 2-[3-hydroxy-4-(3H-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound OC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 JSRSBSWAHZYEMV-UHFFFAOYSA-N 0.000 description 1
- FWWIPQBDURMHHB-UHFFFAOYSA-N ethyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 FWWIPQBDURMHHB-UHFFFAOYSA-N 0.000 description 1
- MKRDNSPNWCLSGO-UHFFFAOYSA-N ethyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-prop-2-ynoxyphenoxy]acetate Chemical compound C#CCOC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 MKRDNSPNWCLSGO-UHFFFAOYSA-N 0.000 description 1
- BAJCEDTWJGFYQW-UHFFFAOYSA-N ethyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C1=NC2=NC=CC=C2N1 BAJCEDTWJGFYQW-UHFFFAOYSA-N 0.000 description 1
- YNTAJEHJUJVUFA-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 YNTAJEHJUJVUFA-UHFFFAOYSA-N 0.000 description 1
- UXCDUWWSFZESBJ-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfanylacetate Chemical compound COC1=CC(SCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 UXCDUWWSFZESBJ-UHFFFAOYSA-N 0.000 description 1
- BLADJENBLUGMKK-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-prop-2-ynoxyphenoxy]acetate Chemical compound C#CCOC1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 BLADJENBLUGMKK-UHFFFAOYSA-N 0.000 description 1
- ZVIOMFISWGGZDV-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 ZVIOMFISWGGZDV-UHFFFAOYSA-N 0.000 description 1
- GHMSTSWKMMLETB-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 GHMSTSWKMMLETB-UHFFFAOYSA-N 0.000 description 1
- PPXKKVGGQYPEAE-UHFFFAOYSA-N ethyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound C1=CC(S(=O)CC(=O)OCC)=CC=C1C1=NC2=CN=CC=C2N1 PPXKKVGGQYPEAE-UHFFFAOYSA-N 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MZRUDWVSYODVEA-UHFFFAOYSA-N methyl 2-[2-(1h-imidazo[4,5-b]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]acetate Chemical compound COC(=O)COC1=CC(OCC#C)=CC=C1C1=NC2=NC=CC=C2N1 MZRUDWVSYODVEA-UHFFFAOYSA-N 0.000 description 1
- AISVDMZCYKXQCM-UHFFFAOYSA-N methyl 2-[2-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC=C1C1=NC2=NC=CC=C2N1 AISVDMZCYKXQCM-UHFFFAOYSA-N 0.000 description 1
- JXOXMRVIUXTRGP-UHFFFAOYSA-N methyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)-5-prop-2-ynoxyphenoxy]acetate Chemical compound COC(=O)COC1=CC(OCC#C)=CC=C1C1=NC2=CN=CC=C2N1 JXOXMRVIUXTRGP-UHFFFAOYSA-N 0.000 description 1
- XOWRYYXLTDYCQH-UHFFFAOYSA-N methyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC=C1C1=NC2=CN=CC=C2N1 XOWRYYXLTDYCQH-UHFFFAOYSA-N 0.000 description 1
- KMZVDDMAKGIMHR-UHFFFAOYSA-N methyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetate Chemical compound COC(=O)CSC1=CC=CC=C1C1=NC2=CN=CC=C2N1 KMZVDDMAKGIMHR-UHFFFAOYSA-N 0.000 description 1
- YKPIGYZSSHHLDR-UHFFFAOYSA-N methyl 2-[2-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound COC(=O)CS(=O)C1=CC=CC=C1C1=NC2=CN=CC=C2N1 YKPIGYZSSHHLDR-UHFFFAOYSA-N 0.000 description 1
- JHMCSXQRMADHMN-UHFFFAOYSA-N methyl 2-[3-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(C=2NC3=CC=CN=C3N=2)=C1 JHMCSXQRMADHMN-UHFFFAOYSA-N 0.000 description 1
- YAMVPHZILUCYLK-UHFFFAOYSA-N methyl 2-[3-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound COC(=O)CS(=O)C1=CC=CC(C=2NC3=CC=NC=C3N=2)=C1 YAMVPHZILUCYLK-UHFFFAOYSA-N 0.000 description 1
- LMHANVSUBOKOHZ-UHFFFAOYSA-N methyl 2-[3-ethoxy-4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 LMHANVSUBOKOHZ-UHFFFAOYSA-N 0.000 description 1
- NOGNGPCXRRSKAT-UHFFFAOYSA-N methyl 2-[3-ethoxy-4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound CCOC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 NOGNGPCXRRSKAT-UHFFFAOYSA-N 0.000 description 1
- BGGGRNUKVYBTSZ-UHFFFAOYSA-N methyl 2-[3-hydroxy-4-(1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound OC1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 BGGGRNUKVYBTSZ-UHFFFAOYSA-N 0.000 description 1
- HTLRRFQOWFOKIY-UHFFFAOYSA-N methyl 2-[3-hydroxy-4-(3H-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound OC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 HTLRRFQOWFOKIY-UHFFFAOYSA-N 0.000 description 1
- USTQNXPFMHNYIM-UHFFFAOYSA-N methyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-(2-methoxy-2-oxoethoxy)phenoxy]acetate Chemical compound COC(=O)COC1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 USTQNXPFMHNYIM-UHFFFAOYSA-N 0.000 description 1
- OIIQESBHUHKJNF-UHFFFAOYSA-N methyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 OIIQESBHUHKJNF-UHFFFAOYSA-N 0.000 description 1
- MMJHUGZFPGMQEX-UHFFFAOYSA-N methyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)-3-prop-2-ynoxyphenoxy]acetate Chemical compound C#CCOC1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 MMJHUGZFPGMQEX-UHFFFAOYSA-N 0.000 description 1
- CHOWEDYKKBOENI-UHFFFAOYSA-N methyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C1=NC2=NC=CC=C2N1 CHOWEDYKKBOENI-UHFFFAOYSA-N 0.000 description 1
- AFCYNKXCPCFGFC-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-(2-methoxy-2-oxoethoxy)phenoxy]acetate Chemical compound COC(=O)COC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 AFCYNKXCPCFGFC-UHFFFAOYSA-N 0.000 description 1
- LCFIMOOZFYGULQ-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 LCFIMOOZFYGULQ-UHFFFAOYSA-N 0.000 description 1
- AVATYEGESJYJBQ-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfanylacetate Chemical compound COC1=CC(SCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 AVATYEGESJYJBQ-UHFFFAOYSA-N 0.000 description 1
- HPMMAGGBPXSPPV-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-methoxyphenyl]sulfinylacetate Chemical compound COC1=CC(S(=O)CC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 HPMMAGGBPXSPPV-UHFFFAOYSA-N 0.000 description 1
- YCKMJQSGJYRNEI-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)-3-prop-2-ynoxyphenoxy]acetate Chemical compound C#CCOC1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 YCKMJQSGJYRNEI-UHFFFAOYSA-N 0.000 description 1
- LDWWJMFCFOEQHC-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 LDWWJMFCFOEQHC-UHFFFAOYSA-N 0.000 description 1
- YOYZVIBLARDBKN-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 YOYZVIBLARDBKN-UHFFFAOYSA-N 0.000 description 1
- DKZBIBRGGXXSAY-UHFFFAOYSA-N methyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenyl]sulfinylacetate Chemical compound C1=CC(S(=O)CC(=O)OC)=CC=C1C1=NC2=CN=CC=C2N1 DKZBIBRGGXXSAY-UHFFFAOYSA-N 0.000 description 1
- MUOXLIQHDGRLBS-UHFFFAOYSA-N methyl 2-hydroxy-4-prop-2-ynoxybenzoate Chemical compound COC(=O)C1=CC=C(OCC#C)C=C1O MUOXLIQHDGRLBS-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 244000309715 mini pig Species 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- MEQYXYZLLOZUJK-UHFFFAOYSA-N n-(2-aminopyridin-3-yl)-2-methoxy-4-prop-2-ynoxybenzamide Chemical compound COC1=CC(OCC#C)=CC=C1C(=O)NC1=CC=CN=C1N MEQYXYZLLOZUJK-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- MLPSIVWITCFCES-UHFFFAOYSA-N pentyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCCCCC)=CC=C1C1=NC2=NC=CC=C2N1 MLPSIVWITCFCES-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- JHFWCLTVWBHEGS-UHFFFAOYSA-N propyl 2-[4-(1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCCC)=CC=C1C1=NC2=NC=CC=C2N1 JHFWCLTVWBHEGS-UHFFFAOYSA-N 0.000 description 1
- TXYUEFRECRJEKZ-UHFFFAOYSA-N propyl 2-[4-(3h-imidazo[4,5-c]pyridin-2-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCCC)=CC=C1C1=NC2=CN=CC=C2N1 TXYUEFRECRJEKZ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19813132754 DE3132754A1 (de) | 1981-08-19 | 1981-08-19 | "2-aryl-imidazo(4,5-b)pyridine, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung" |
DE3132754.0 | 1981-08-19 | ||
DE3139064.1 | 1981-10-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5839681A JPS5839681A (ja) | 1983-03-08 |
JPH046713B2 true JPH046713B2 (de) | 1992-02-06 |
Family
ID=6139637
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57142733A Granted JPS5839681A (ja) | 1981-08-19 | 1982-08-19 | 2−アリ−ルイミダゾピリジン化合物 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JPS5839681A (de) |
DE (1) | DE3132754A1 (de) |
ZA (1) | ZA825968B (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007063225A (ja) * | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS49102693A (de) * | 1973-02-03 | 1974-09-27 | ||
JPS5625179A (en) * | 1979-07-11 | 1981-03-10 | Thomae Gmbh Dr K | Novel imidazopyridine compound |
-
1981
- 1981-08-19 DE DE19813132754 patent/DE3132754A1/de not_active Withdrawn
-
1982
- 1982-08-17 ZA ZA825968A patent/ZA825968B/xx unknown
- 1982-08-19 JP JP57142733A patent/JPS5839681A/ja active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS49102693A (de) * | 1973-02-03 | 1974-09-27 | ||
JPS5625179A (en) * | 1979-07-11 | 1981-03-10 | Thomae Gmbh Dr K | Novel imidazopyridine compound |
Also Published As
Publication number | Publication date |
---|---|
DE3132754A1 (de) | 1983-03-03 |
ZA825968B (en) | 1983-07-27 |
JPS5839681A (ja) | 1983-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5104881A (en) | 2-arylimidazopyridines | |
NL9201237A (nl) | 3,4-digesubstitueerde-1,2,5-thiadiazool-1-oxyden en 1,1-dioxyden. | |
JPH0314811B2 (de) | ||
HU211163A9 (en) | Substituted salicylic acids | |
JP2021501184A (ja) | P2x3及び/又はp2x2/3受容体アンタゴニスト、それを含む医薬組成物及びその使用 | |
KR910002824B1 (ko) | 피리딘유도체 및 그것을 함유하는 궤양치료제 | |
JPH03388B2 (de) | ||
US4477454A (en) | 2-Aryltetraazaindenes for treating cardiac insufficiency | |
NO823026L (no) | 2(1h)-pyridinoner og fremgangsmaate for deres fremstilling | |
KR100194993B1 (ko) | 술폰아미드 유도체 | |
US4818760A (en) | Derivatives of pyridylsulfinyl(benz-or thieno-)imidazoles and their use as gastric secretion inhibiting substances | |
US4980356A (en) | 2-imino-6-polyfluoroalkoxybenzothiazole derivatives, and pharamaceutical compositions containing them and their treatment of medical conditions associated with the effects of glutamate | |
KR840001614B1 (ko) | 4-치환된 피리딘 및 피리미딘 유도체의 제조방법 | |
WO2023160672A1 (en) | Compounds and compositions for treating conditions associated with lpa receptor activity | |
JPH046713B2 (de) | ||
JPH03501609A (ja) | 新規ベンゾイミダゾール誘導体 | |
US4346221A (en) | Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from 6-(pyridinyl)-3(2H)-pyridazinones | |
US4305943A (en) | 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics | |
US4778803A (en) | Nitrogen-arylmethoxy-thiophene derivatives and acid addition salts thereof, and pharmaceutical preparations containing these compounds | |
US4304776A (en) | 4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as intermediates and cardiotonics | |
US4338446A (en) | Di-(lower-alkyl)hydroxy-[2-oxo-2-(pyridinyl)ethyl]-propanedioates | |
WO2024112895A1 (en) | Compounds and compositions for treating conditions associated with lpa receptor activity | |
JPS63179840A (ja) | 新規化学物質 | |
EP0150463A1 (de) | Substituierte 4,5-Dihydro-7-Vinyl-3(2H) Pyridazinone und 6-Vinyl-3(2H) Pyridazinone und Verfahren zu ihrer Herstellung | |
EP0639975A1 (de) | Heterocyclisch substituierte pyridin-derivate und anwendungen |