DE69230163T2 - Thiazolylbenzofuranderivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten - Google Patents

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Publication number

DE69230163T2

DE69230163T2 DE69230163T DE69230163T DE69230163T2 DE 69230163 T2 DE69230163 T2 DE 69230163T2 DE 69230163 T DE69230163 T DE 69230163T DE 69230163 T DE69230163 T DE 69230163T DE 69230163 T2 DE69230163 T2 DE 69230163T2

Authority

DE

Germany

Prior art keywords

alkyl

compound

salt

formula

substituted

Prior art date

1991-08-16

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 - Fee Related

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• 238000000034 method Methods 0.000 title claims abstract description 109
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
• 238000002360 preparation method Methods 0.000 title abstract description 24
• IQDNFLQNJPENQU-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1,3-thiazole Chemical class C1=CSC(C=2OC3=CC=CC=C3C=2)=N1 IQDNFLQNJPENQU-UHFFFAOYSA-N 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 320
• 150000003839 salts Chemical class 0.000 claims abstract description 239
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 122
• -1 cyano, hydroxy Chemical group 0.000 claims abstract description 112
• 125000003118 aryl group Chemical group 0.000 claims abstract description 90
• 125000002252 acyl group Chemical group 0.000 claims abstract description 84
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 64
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 45
• 150000002367 halogens Chemical group 0.000 claims abstract description 45
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 239000001257 hydrogen Substances 0.000 claims abstract description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
• 125000005843 halogen group Chemical group 0.000 claims abstract description 18
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract description 15
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
• 125000004429 atom Chemical group 0.000 claims abstract description 10
• 125000001424 substituent group Chemical group 0.000 claims abstract description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
• 239000000203 mixture Substances 0.000 claims description 116
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 105
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 69
• 239000002253 acid Substances 0.000 claims description 43
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 8
• 230000007062 hydrolysis Effects 0.000 claims description 8
• 238000006460 hydrolysis reaction Methods 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 7
• 238000010531 catalytic reduction reaction Methods 0.000 claims description 7
• 239000003638 chemical reducing agent Substances 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 6
• SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
• 125000003435 aroyl group Chemical group 0.000 claims description 5
• 206010020751 Hypersensitivity Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 150000001356 alkyl thiols Chemical class 0.000 claims description 4
• 230000007815 allergy Effects 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 238000007363 ring formation reaction Methods 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000005425 toluyl group Chemical group 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• QALVWRPQKALRFR-UHFFFAOYSA-N 4-tert-butyl-2-[5-[[2-(2h-tetrazol-5-ylmethyl)phenyl]methoxy]-1-benzofuran-2-yl]-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CC=4NN=NN=4)C=C3C=2)=N1 QALVWRPQKALRFR-UHFFFAOYSA-N 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
• 150000003973 alkyl amines Chemical class 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 230000002140 halogenating effect Effects 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 159000000000 sodium salts Chemical class 0.000 claims description 3
• PSILZZNMGXTOOP-UHFFFAOYSA-N 2-[2-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]oxymethyl]phenyl]acetic acid Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CC(O)=O)C=C3C=2)=N1 PSILZZNMGXTOOP-UHFFFAOYSA-N 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
• 238000005917 acylation reaction Methods 0.000 claims description 2
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
• 238000006900 dealkylation reaction Methods 0.000 claims description 2
• 238000007257 deesterification reaction Methods 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims description 2
• 125000004970 halomethyl group Chemical group 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 15
• 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 6
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 6
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
• 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
• 150000004684 trihydrates Chemical class 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 abstract description 25
• 125000003545 alkoxy group Chemical group 0.000 abstract description 7
• 125000003282 alkyl amino group Chemical group 0.000 abstract description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 6
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract description 6
• 125000003342 alkenyl group Chemical group 0.000 abstract description 5
• 125000004450 alkenylene group Chemical group 0.000 abstract description 5
• 125000002947 alkylene group Chemical group 0.000 abstract description 5
• 150000002431 hydrogen Chemical class 0.000 abstract 1
• 229910052727 yttrium Inorganic materials 0.000 abstract 1
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 198
• 238000006243 chemical reaction Methods 0.000 description 176
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
• 238000002844 melting Methods 0.000 description 84
• 230000008018 melting Effects 0.000 description 84
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• 239000002585 base Substances 0.000 description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
• 239000002904 solvent Substances 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• 238000001816 cooling Methods 0.000 description 40
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• 239000000243 solution Substances 0.000 description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 238000001914 filtration Methods 0.000 description 25
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 230000002411 adverse Effects 0.000 description 24
• 239000012267 brine Substances 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
• 239000006188 syrup Substances 0.000 description 23
• 235000020357 syrup Nutrition 0.000 description 23
• 238000010792 warming Methods 0.000 description 21
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 229910052783 alkali metal Inorganic materials 0.000 description 18
• 238000004440 column chromatography Methods 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 238000003756 stirring Methods 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
• 239000002244 precipitate Substances 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 239000005457 ice water Substances 0.000 description 15
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 229910052751 metal Inorganic materials 0.000 description 14
• 239000002184 metal Substances 0.000 description 14
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 13
• 239000003921 oil Substances 0.000 description 12
• 239000003960 organic solvent Substances 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
• 238000010438 heat treatment Methods 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• 150000001342 alkaline earth metals Chemical class 0.000 description 9
• 239000013078 crystal Substances 0.000 description 9
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 229910052697 platinum Inorganic materials 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 150000001340 alkali metals Chemical class 0.000 description 7
• 238000000354 decomposition reaction Methods 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 239000008096 xylene Substances 0.000 description 7
• 201000004624 Dermatitis Diseases 0.000 description 6
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 235000011054 acetic acid Nutrition 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 229910017052 cobalt Inorganic materials 0.000 description 6
• 239000010941 cobalt Substances 0.000 description 6
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
• 229910052802 copper Inorganic materials 0.000 description 6
• 239000010949 copper Substances 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
• YXRUWYWSPZHKLD-UHFFFAOYSA-N 2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-carbaldehyde Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(C=O)C=C3C=2)=N1 YXRUWYWSPZHKLD-UHFFFAOYSA-N 0.000 description 5
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
• 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 5
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
• 150000008065 acid anhydrides Chemical class 0.000 description 5
• 239000011575 calcium Substances 0.000 description 5
• 229910052791 calcium Inorganic materials 0.000 description 5
• 125000001589 carboacyl group Chemical group 0.000 description 5
• 238000006757 chemical reactions by type Methods 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 239000011777 magnesium Substances 0.000 description 5
• 229910052749 magnesium Inorganic materials 0.000 description 5
• 239000012528 membrane Substances 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• 239000011591 potassium Substances 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 235000009518 sodium iodide Nutrition 0.000 description 5
• BNALANGFESRXOP-UHFFFAOYSA-N 2-[2-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]oxymethyl]phenyl]acetonitrile Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CC#N)C=C3C=2)=N1 BNALANGFESRXOP-UHFFFAOYSA-N 0.000 description 4
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
• CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 4
• PNZYQVLBRDFJLB-UHFFFAOYSA-N 4-tert-butyl-2-[5-(chloromethyl)-1-benzofuran-2-yl]-1,3-thiazole Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(CCl)C=C3C=2)=N1 PNZYQVLBRDFJLB-UHFFFAOYSA-N 0.000 description 4
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• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
• UXBJXJHRVOEYPA-UHFFFAOYSA-N n,n-dimethyl-3-sulfanylpropanamide Chemical compound CN(C)C(=O)CCS UXBJXJHRVOEYPA-UHFFFAOYSA-N 0.000 description 1
• VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
• PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
• JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
• QLVFXBSHXBMJMU-UHFFFAOYSA-N n-tert-butyl-n-[[2-(5-hydroxy-1-benzofuran-2-yl)-1,3-thiazol-4-yl]methyl]acetamide Chemical compound CC(=O)N(C(C)(C)C)CC1=CSC(C=2OC3=CC=C(O)C=C3C=2)=N1 QLVFXBSHXBMJMU-UHFFFAOYSA-N 0.000 description 1
• WYLAJBGOOAKMAP-UHFFFAOYSA-N n-tert-butyl-n-[[2-[5-[[2-(chloromethyl)phenyl]methoxy]-1-benzofuran-2-yl]-1,3-thiazol-4-yl]methyl]acetamide Chemical compound CC(=O)N(C(C)(C)C)CC1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CCl)C=C3C=2)=N1 WYLAJBGOOAKMAP-UHFFFAOYSA-N 0.000 description 1
• YWORNCVWQMGRQA-UHFFFAOYSA-N n-tert-butyl-n-[[2-[5-[[2-(cyanomethyl)phenyl]methoxy]-1-benzofuran-2-yl]-1,3-thiazol-4-yl]methyl]acetamide Chemical compound CC(=O)N(C(C)(C)C)CC1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CC#N)C=C3C=2)=N1 YWORNCVWQMGRQA-UHFFFAOYSA-N 0.000 description 1
• ZFIFHAKCBWOSRN-UHFFFAOYSA-N naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 ZFIFHAKCBWOSRN-UHFFFAOYSA-N 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 229940100684 pentylamine Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000004714 phosphonium salts Chemical class 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• 150000003018 phosphorus compounds Chemical class 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-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
• TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000011946 reduction process Methods 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 229910052718 tin Inorganic materials 0.000 description 1
• 239000011135 tin Substances 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 210000003437 trachea Anatomy 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 125000005023 xylyl group Chemical group 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1