NO317631B1 - Oksygeninneholdende heterocykliske forbindelser - Google Patents

Info

Publication number

NO317631B1

NO317631B1 NO19970151A NO970151A NO317631B1 NO 317631 B1 NO317631 B1 NO 317631B1 NO 19970151 A NO19970151 A NO 19970151A NO 970151 A NO970151 A NO 970151A NO 317631 B1 NO317631 B1 NO 317631B1

Authority

NO

Norway

Prior art keywords

compound

substituted

methoxy

nmr

ppm

Prior art date

1995-05-19

Links

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• 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 21
• 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 11
• 239000001301 oxygen Substances 0.000 title claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
• 239000001257 hydrogen Substances 0.000 claims abstract description 47
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 44
• 125000003118 aryl group Chemical group 0.000 claims abstract description 40
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 40
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
• 150000002367 halogens Chemical class 0.000 claims abstract description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
• 150000001721 carbon Chemical group 0.000 claims abstract description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 4
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims abstract description 4
• -1 quinozolinyl Chemical group 0.000 claims description 35
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 238000002360 preparation method Methods 0.000 claims description 22
• 125000001589 carboacyl group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 230000002757 inflammatory effect Effects 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 208000026935 allergic disease Diseases 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 3
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
• 125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 908
• 238000000034 method Methods 0.000 description 295
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 185
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 183
• 239000000203 mixture Substances 0.000 description 178
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
• 238000002844 melting Methods 0.000 description 169
• 230000008018 melting Effects 0.000 description 169
• 239000000243 solution Substances 0.000 description 152
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 138
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 136
• 239000013078 crystal Substances 0.000 description 134
• 239000002904 solvent Substances 0.000 description 129
• 238000000921 elemental analysis Methods 0.000 description 126
• 238000003756 stirring Methods 0.000 description 117
• 239000000126 substance Substances 0.000 description 112
• 239000007787 solid Substances 0.000 description 111
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• 238000006243 chemical reaction Methods 0.000 description 91
• 239000012044 organic layer Substances 0.000 description 87
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 78
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 76
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 238000010898 silica gel chromatography Methods 0.000 description 74
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 73
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 69
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
• 230000002829 reductive effect Effects 0.000 description 57
• 238000001816 cooling Methods 0.000 description 50
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 239000012442 inert solvent Substances 0.000 description 48
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
• 238000000605 extraction Methods 0.000 description 44
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 38
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 36
• 239000007864 aqueous solution Substances 0.000 description 36
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 36
• 230000008569 process Effects 0.000 description 33
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 29
• 238000010992 reflux Methods 0.000 description 28
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 26
• 238000009835 boiling Methods 0.000 description 26
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 239000012300 argon atmosphere Substances 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• XSIHTGSZVFKCNB-UHFFFAOYSA-N 2-[4-[(3,5-dichloropyridin-4-yl)carbamoyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=2C(CC(O)=O)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl XSIHTGSZVFKCNB-UHFFFAOYSA-N 0.000 description 22
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 22
• 238000010438 heat treatment Methods 0.000 description 21
• 238000001914 filtration Methods 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 19
• 229920006395 saturated elastomer Polymers 0.000 description 19
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 19
• 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
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 16
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 16
• 239000003377 acid catalyst Substances 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• 239000000706 filtrate Substances 0.000 description 15
• 235000017557 sodium bicarbonate Nutrition 0.000 description 15
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
• 238000007796 conventional method Methods 0.000 description 13
• 239000000741 silica gel Substances 0.000 description 13
• 229910002027 silica gel Inorganic materials 0.000 description 13
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 12
• 229910015900 BF3 Inorganic materials 0.000 description 11
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• 229940098779 methanesulfonic acid Drugs 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• QYOUBIYWOYGIQG-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)ethanol Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(O)CC1=C(Cl)C=NC=C1Cl QYOUBIYWOYGIQG-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 239000003814 drug Substances 0.000 description 8
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
• 206010006482 Bronchospasm Diseases 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• RIEKUNSZSAGWMV-UHFFFAOYSA-N methyl 2,2-diethyl-7-methoxy-3h-1-benzofuran-4-carboxylate Chemical compound COC1=CC=C(C(=O)OC)C2=C1OC(CC)(CC)C2 RIEKUNSZSAGWMV-UHFFFAOYSA-N 0.000 description 7
• LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• TVBIIGMNGQNEIR-UHFFFAOYSA-N 1-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)-2-pyridin-4-ylethanol Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(O)CC1=CC=NC=C1 TVBIIGMNGQNEIR-UHFFFAOYSA-N 0.000 description 6
• BKZNPJJHZSUNLN-UHFFFAOYSA-N 1-(7-methoxy-3-methyl-2,3-dihydro-1-benzofuran-4-yl)-2-pyridin-4-ylethanol Chemical compound C1=2C(C)COC=2C(OC)=CC=C1C(O)CC1=CC=NC=C1 BKZNPJJHZSUNLN-UHFFFAOYSA-N 0.000 description 6
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
• GNFGRSPDOZRGOT-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(7-methoxy-3-methyl-2,3-dihydro-1-benzofuran-4-yl)ethanol Chemical compound C1=2C(C)COC=2C(OC)=CC=C1C(O)CC1=C(Cl)C=NC=C1Cl GNFGRSPDOZRGOT-UHFFFAOYSA-N 0.000 description 6
• WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 230000002152 alkylating effect Effects 0.000 description 6
• 230000007885 bronchoconstriction Effects 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 230000001413 cellular effect Effects 0.000 description 6
• 239000003638 chemical reducing agent Substances 0.000 description 6
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• QSTNLQHRINHPQI-UHFFFAOYSA-N ethyl 2-[4-(cyclohexylcarbamoyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound CCOC(=O)CC1COC(C(=CC=2)OC)=C1C=2C(=O)NC1CCCCC1 QSTNLQHRINHPQI-UHFFFAOYSA-N 0.000 description 6
• 238000005984 hydrogenation reaction Methods 0.000 description 6
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