JPH053468B2 - - Google Patents
Info
- Publication number
- JPH053468B2 JPH053468B2 JP7781984A JP7781984A JPH053468B2 JP H053468 B2 JPH053468 B2 JP H053468B2 JP 7781984 A JP7781984 A JP 7781984A JP 7781984 A JP7781984 A JP 7781984A JP H053468 B2 JPH053468 B2 JP H053468B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyridyl
- substituent
- melting point
- 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
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 methylenedioxy group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000003699 antiulcer agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 238000002844 melting Methods 0.000 description 44
- 230000008018 melting Effects 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZEDZSJVLMNQCDQ-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-2-pyridin-3-ylethanone;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1C(=O)C(Br)C1=CC=CN=C1 ZEDZSJVLMNQCDQ-UHFFFAOYSA-N 0.000 description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 239000002221 antipyretic Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- RHBGITBPARBDPH-ZPUQHVIOSA-N (E,E)-piperic acid Chemical compound OC(=O)\C=C\C=C\C1=CC=C2OCOC2=C1 RHBGITBPARBDPH-ZPUQHVIOSA-N 0.000 description 2
- JPEZMIFKLNWZTB-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-2-pyridin-3-ylethanone Chemical compound C=1C=C2CCCC2=CC=1C(=O)CC1=CC=CN=C1 JPEZMIFKLNWZTB-UHFFFAOYSA-N 0.000 description 2
- OGKXSQRUMNMIJK-UHFFFAOYSA-N 2-bromo-1-(2,3-dihydro-1h-inden-5-yl)-2-pyridin-3-ylethanone Chemical compound C=1C=C2CCCC2=CC=1C(=O)C(Br)C1=CC=CN=C1 OGKXSQRUMNMIJK-UHFFFAOYSA-N 0.000 description 2
- WXUCODGDMJORCX-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(Br)C1=CC=CN=C1 WXUCODGDMJORCX-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NUYXENDTGLIWDX-UHFFFAOYSA-N 4-(4-methoxyphenyl)-5-pyridin-3-yl-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=NC=CC=2)SC(N)=N1 NUYXENDTGLIWDX-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- RGXHFNJJWXTYFT-UHFFFAOYSA-N 5-pyridin-2-yl-1,3-thiazole Chemical class S1C=NC=C1C1=CC=CC=N1 RGXHFNJJWXTYFT-UHFFFAOYSA-N 0.000 description 2
- REJOECPUMPPMTC-UHFFFAOYSA-N 5-pyridin-3-yl-1,3-thiazole Chemical compound S1C=NC=C1C1=CC=CN=C1 REJOECPUMPPMTC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- UEOFNBCUGJADBM-UHFFFAOYSA-N Ethyl 3,4,5-trimethoxybenzoate Chemical compound CCOC(=O)C1=CC(OC)=C(OC)C(OC)=C1 UEOFNBCUGJADBM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- SROLLKZMNPYRBY-UHFFFAOYSA-N benzyl n-[[4-(4-methoxyphenyl)-5-pyridin-3-yl-1,3-thiazol-2-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=NC=CC=2)SC(CNC(=O)OCC=2C=CC=CC=2)=N1 SROLLKZMNPYRBY-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- QMBOGHRCVUZBIR-UHFFFAOYSA-N methyl 2,3-dihydro-1h-indene-5-carboxylate Chemical compound COC(=O)C1=CC=C2CCCC2=C1 QMBOGHRCVUZBIR-UHFFFAOYSA-N 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TWRFUNKGACNVQD-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-bromo-2-pyridin-3-ylethanone Chemical compound C=1C=C2OCOC2=CC=1C(=O)C(Br)C1=CC=CN=C1 TWRFUNKGACNVQD-UHFFFAOYSA-N 0.000 description 1
- VWDDEIVOSXIFOB-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-pyridin-3-ylethanone Chemical compound C=1C=C2OCOC2=CC=1C(=O)CC1=CC=CN=C1 VWDDEIVOSXIFOB-UHFFFAOYSA-N 0.000 description 1
- CYLUJNVQHKFWTG-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-pyridin-3-ylpropan-2-one Chemical compound C=1C=C2OCOC2=CC=1CC(=O)CC1=CC=CN=C1 CYLUJNVQHKFWTG-UHFFFAOYSA-N 0.000 description 1
- RRYFWOWLIAHFTF-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2-pyridin-3-ylethanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)CC1=CC=CN=C1 RRYFWOWLIAHFTF-UHFFFAOYSA-N 0.000 description 1
- SNRXHZHOTNCTNN-UHFFFAOYSA-N 1-(4-ethylphenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(CC)=CC=C1C(=O)CC1=CC=CN=C1 SNRXHZHOTNCTNN-UHFFFAOYSA-N 0.000 description 1
- DNOLYZHTKURJIV-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1=CC=CN=C1 DNOLYZHTKURJIV-UHFFFAOYSA-N 0.000 description 1
- YDDIGUFGIDJEEM-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyridin-2-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CC1=CC=CC=N1 YDDIGUFGIDJEEM-UHFFFAOYSA-N 0.000 description 1
- NDBVHXUNBUTGKJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CC1=CC=CN=C1 NDBVHXUNBUTGKJ-UHFFFAOYSA-N 0.000 description 1
- FQOSOMYMMDPZAA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyridin-4-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CC1=CC=NC=C1 FQOSOMYMMDPZAA-UHFFFAOYSA-N 0.000 description 1
- HQFISWJGKRAAFU-UHFFFAOYSA-N 1-[4-(methoxymethoxy)phenyl]-2-pyridin-3-ylethanone Chemical compound C1=CC(OCOC)=CC=C1C(=O)CC1=CC=CN=C1 HQFISWJGKRAAFU-UHFFFAOYSA-N 0.000 description 1
- BHTURNCRHPDYCF-UHFFFAOYSA-N 1-naphthalen-2-yl-2-pyridin-3-ylethanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)CC1=CC=CN=C1 BHTURNCRHPDYCF-UHFFFAOYSA-N 0.000 description 1
- CMOXTMGJZNCXEI-UHFFFAOYSA-N 1-phenyl-2-pyridin-2-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=N1 CMOXTMGJZNCXEI-UHFFFAOYSA-N 0.000 description 1
- DDEBMFBOWGAMAX-UHFFFAOYSA-N 1-phenyl-2-pyridin-3-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CN=C1 DDEBMFBOWGAMAX-UHFFFAOYSA-N 0.000 description 1
- ACULMSXMKICJIS-UHFFFAOYSA-N 1-phenyl-2-pyridin-4-ylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=NC=C1 ACULMSXMKICJIS-UHFFFAOYSA-N 0.000 description 1
- NVGPNJNFXRISQH-UHFFFAOYSA-N 1-pyridin-1-ium-3-ylethanone;bromide Chemical compound [Br-].CC(=O)C1=CC=C[NH+]=C1 NVGPNJNFXRISQH-UHFFFAOYSA-N 0.000 description 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 1
- SFLKCYWGQJJTAL-UHFFFAOYSA-N 2-(5-methylpyridin-3-yl)-1-phenylethanone Chemical compound CC1=CN=CC(CC(=O)C=2C=CC=CC=2)=C1 SFLKCYWGQJJTAL-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZYKJENJDMYBNJP-UHFFFAOYSA-N 2-bromo-1-(3,4-dimethoxyphenyl)-2-pyridin-3-ylethanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C(Br)C1=CC=CN=C1 ZYKJENJDMYBNJP-UHFFFAOYSA-N 0.000 description 1
- PZPXCQUSBYKWLE-UHFFFAOYSA-N 2-bromo-1-(4-ethylphenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(CC)=CC=C1C(=O)C(Br)C1=CC=CN=C1 PZPXCQUSBYKWLE-UHFFFAOYSA-N 0.000 description 1
- JBYXKOGEXFSTSP-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(F)=CC=C1C(=O)C(Br)C1=CC=CN=C1 JBYXKOGEXFSTSP-UHFFFAOYSA-N 0.000 description 1
- COYCTTRTOHFCQY-UHFFFAOYSA-N 2-bromo-1-(4-hydroxyphenyl)-2-pyridin-3-ylethanone Chemical compound C1=CC(O)=CC=C1C(=O)C(Br)C1=CC=CN=C1 COYCTTRTOHFCQY-UHFFFAOYSA-N 0.000 description 1
- NEZRNMJDEVSTRB-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-2-pyridin-2-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(Br)C1=CC=CC=N1 NEZRNMJDEVSTRB-UHFFFAOYSA-N 0.000 description 1
- MSQHIFUAMYWZMN-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)-2-pyridin-4-ylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(Br)C1=CC=NC=C1 MSQHIFUAMYWZMN-UHFFFAOYSA-N 0.000 description 1
- FYSKSZILWCRHNL-UHFFFAOYSA-N 2-bromo-1-phenyl-2-pyridin-2-ylethanone Chemical compound C=1C=CC=NC=1C(Br)C(=O)C1=CC=CC=C1 FYSKSZILWCRHNL-UHFFFAOYSA-N 0.000 description 1
- VNVGJDKHFJLKSU-UHFFFAOYSA-N 2-bromo-1-phenyl-2-pyridin-3-ylethanone Chemical compound C=1C=CN=CC=1C(Br)C(=O)C1=CC=CC=C1 VNVGJDKHFJLKSU-UHFFFAOYSA-N 0.000 description 1
- HCXDYMDEHQTSJH-UHFFFAOYSA-N 2-bromo-1-phenyl-2-pyridin-4-ylethanone Chemical compound C=1C=NC=CC=1C(Br)C(=O)C1=CC=CC=C1 HCXDYMDEHQTSJH-UHFFFAOYSA-N 0.000 description 1
- QCFVKNXEWKLYMY-UHFFFAOYSA-N 2-bromo-2-(5-methylpyridin-3-yl)-1-phenylethanone Chemical compound CC1=CN=CC(C(Br)C(=O)C=2C=CC=CC=2)=C1 QCFVKNXEWKLYMY-UHFFFAOYSA-N 0.000 description 1
- LSLAAJZAYBJRSU-UHFFFAOYSA-N 2-bromo-2-pyridin-3-yl-1-(3,4,5-trimethoxyphenyl)ethanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C(Br)C=2C=NC=CC=2)=C1 LSLAAJZAYBJRSU-UHFFFAOYSA-N 0.000 description 1
- SMHAPCQDIOZYPZ-UHFFFAOYSA-N 2-cyclohexyl-4-(4-methoxyphenyl)-5-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=NC=CC=2)SC(C2CCCCC2)=N1 SMHAPCQDIOZYPZ-UHFFFAOYSA-N 0.000 description 1
- ROGFAYBYBRPGNJ-UHFFFAOYSA-N 2-cyclohexyl-4-phenyl-5-pyridin-3-yl-1,3-thiazole Chemical compound C1CCCCC1C1=NC(C=2C=CC=CC=2)=C(C=2C=NC=CC=2)S1 ROGFAYBYBRPGNJ-UHFFFAOYSA-N 0.000 description 1
- ABUJRBHPDLEQJL-UHFFFAOYSA-N 2-ethyl-4-(4-methoxyphenyl)-5-pyridin-3-yl-1,3-thiazole Chemical compound S1C(CC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=CN=C1 ABUJRBHPDLEQJL-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 description 1
- VKLVBJCIOOUXOQ-UHFFFAOYSA-N 2-pyridin-3-yl-1-(3,4,5-trimethoxyphenyl)ethanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)CC=2C=NC=CC=2)=C1 VKLVBJCIOOUXOQ-UHFFFAOYSA-N 0.000 description 1
- MDKGFCIBBDLSNM-UHFFFAOYSA-N 2-pyridin-3-yl-1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C=1C=C2CCCCC2=CC=1C(=O)CC1=CC=CN=C1 MDKGFCIBBDLSNM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CYQPBVXPBLGHMU-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-methyl-5-pyridin-3-yl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CN=C1 CYQPBVXPBLGHMU-UHFFFAOYSA-N 0.000 description 1
- NLGAFPPIDFYIAE-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-5-yl)-n-methyl-5-pyridin-3-yl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C=2C=C3CCCC3=CC=2)=C1C1=CC=CN=C1 NLGAFPPIDFYIAE-UHFFFAOYSA-N 0.000 description 1
- USDPJLQQSGAMIJ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-phenyl-5-pyridin-3-yl-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=NC=CC=2)SC(C=2C=CC=CC=2)=N1 USDPJLQQSGAMIJ-UHFFFAOYSA-N 0.000 description 1
- PKDDDTJJMPPYMB-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n-methyl-5-pyridin-3-yl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=CN=C1 PKDDDTJJMPPYMB-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- AYYNUGSDPRDVCH-UHFFFAOYSA-N ethyl 3,4-dimethoxybenzoate Chemical compound CCOC(=O)C1=CC=C(OC)C(OC)=C1 AYYNUGSDPRDVCH-UHFFFAOYSA-N 0.000 description 1
- KWFADUNOPOSMIJ-UHFFFAOYSA-N ethyl 3-chloro-3-oxopropanoate Chemical compound CCOC(=O)CC(Cl)=O KWFADUNOPOSMIJ-UHFFFAOYSA-N 0.000 description 1
- PEGFAXXBTQVMSY-UHFFFAOYSA-N ethyl 4-(methoxymethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCOC)C=C1 PEGFAXXBTQVMSY-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GYUXWAIDEGEMEE-UHFFFAOYSA-N methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate Chemical compound O1CCOC2=CC(C(=O)OC)=CC=C21 GYUXWAIDEGEMEE-UHFFFAOYSA-N 0.000 description 1
- MSEBQGULDWDIRW-UHFFFAOYSA-N methyl 4-fluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1 MSEBQGULDWDIRW-UHFFFAOYSA-N 0.000 description 1
- GKKIDGUCTHRVRV-UHFFFAOYSA-N methyl 5-amino-5-sulfanylidenepentanoate Chemical compound COC(=O)CCCC(N)=S GKKIDGUCTHRVRV-UHFFFAOYSA-N 0.000 description 1
- IODOXLXFXNATGI-UHFFFAOYSA-N methyl naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OC)=CC=C21 IODOXLXFXNATGI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XZAISPXDCGRJJO-UHFFFAOYSA-N n-[2-(methylamino)-2-sulfanylideneethyl]benzamide Chemical compound CNC(=S)CNC(=O)C1=CC=CC=C1 XZAISPXDCGRJJO-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- DBFZMOWIKUYQAP-UHFFFAOYSA-N n-methyl-5-pyridin-3-yl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC=C1C1=CC=CN=C1 DBFZMOWIKUYQAP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- PVIJLUXKGBJNNI-UHFFFAOYSA-N piperazine-1-carbothioamide Chemical compound NC(=S)N1CCNCC1 PVIJLUXKGBJNNI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 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
- 210000002417 xiphoid bone Anatomy 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7781984A JPS6110580A (ja) | 1984-04-17 | 1984-04-17 | ５−ピリジル−１，３−チアゾ−ル誘導体，その製造法およびそれを含んでなる医薬組成物 |
| EP84305789A EP0149884B1 (en) | 1983-09-09 | 1984-08-23 | 5-pyridyl-1,3-thiazole derivatives, their production and use |
| DE8484305789T DE3486009T2 (de) | 1983-09-09 | 1984-08-23 | 5-pyridyl-1,3-thiazol-derivate, ihre herstellung und anwendung. |
| AT84305789T ATE83483T1 (de) | 1983-09-09 | 1984-08-23 | 5-pyridyl-1,3-thiazol-derivate, ihre herstellung und anwendung. |
| AU32433/84A AU567754B2 (en) | 1983-09-09 | 1984-08-27 | 5-pyridyl-1,3-thiazoles |
| US06/647,436 US4612321A (en) | 1983-09-09 | 1984-09-05 | 5-pyridyl-1,3-thiazole derivatives |
| HU843401A HU201753B (en) | 1983-09-09 | 1984-09-07 | Process for producing new 5-pyridyl-1,3-thiazole derivatives and pharmaceutical compositions comprising same as active ingredient |
| CA000462626A CA1255663A (en) | 1983-09-09 | 1984-09-07 | 5-pyridyl-1,3-thiazole derivatives, their production and use |
| KR1019840005499A KR910004430B1 (ko) | 1983-04-17 | 1984-09-08 | 5-피리딜-1,3-티아졸 유도체의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7781984A JPS6110580A (ja) | 1984-04-17 | 1984-04-17 | ５−ピリジル−１，３−チアゾ−ル誘導体，その製造法およびそれを含んでなる医薬組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6110580A JPS6110580A (ja) | 1986-01-18 |
| JPH053468B2 true JPH053468B2 (ko) | 1993-01-14 |
Family
ID=13644638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7781984A Granted JPS6110580A (ja) | 1983-04-17 | 1984-04-17 | ５−ピリジル−１，３−チアゾ−ル誘導体，その製造法およびそれを含んでなる医薬組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6110580A (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001074811A2 (en) * | 2000-03-30 | 2001-10-11 | Takeda Chemical Industries, Ltd. | Substituted 1,3-thiazole compounds, their production and use |
-
1984
- 1984-04-17 JP JP7781984A patent/JPS6110580A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6110580A (ja) | 1986-01-18 |
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