JP2011500537A - Ｈ１受容体アンタゴニストとしてのフタラジンおよびピリド［３，４−ｄ］ピリダジン化合物 - Google Patents

Info

Publication number

JP2011500537A

JP2011500537A JP2010528414A JP2010528414A JP2011500537A JP 2011500537 A JP2011500537 A JP 2011500537A JP 2010528414 A JP2010528414 A JP 2010528414A JP 2010528414 A JP2010528414 A JP 2010528414A JP 2011500537 A JP2011500537 A JP 2011500537A

Authority

JP

Japan

Prior art keywords

methyl

chlorophenyl

formula

pyrrolidinyl

acid

Prior art date

2007-10-11

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.)

Ceased

Links

• Espacenet
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• 102000003834 Histamine H1 Receptors Human genes 0.000 title description 14
• 108090000110 Histamine H1 Receptors Proteins 0.000 title description 14
• 229940044551 receptor antagonist Drugs 0.000 title description 7
• 239000002464 receptor antagonist Substances 0.000 title description 7
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title 1
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title 1
• IHYJXEQIZYROGA-UHFFFAOYSA-N pyrido[3,4-d]pyridazine Chemical class N1=NC=C2C=NC=CC2=C1 IHYJXEQIZYROGA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 239000000203 mixture Substances 0.000 claims abstract description 149
• 150000003839 salts Chemical class 0.000 claims abstract description 86
• 238000000034 method Methods 0.000 claims abstract description 48
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 18
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 17
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 15
• 208000026935 allergic disease Diseases 0.000 claims description 13
• 208000027866 inflammatory disease Diseases 0.000 claims description 13
• 230000002757 inflammatory effect Effects 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 239000003246 corticosteroid Substances 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 229940124597 therapeutic agent Drugs 0.000 claims description 7
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 6
• 229960001334 corticosteroids Drugs 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• YXICCMIPIPEESR-DENIHFKCSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3r)-3-ethylsulfonylbutyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)[C@H](C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-DENIHFKCSA-N 0.000 claims description 3
• YXICCMIPIPEESR-SIKLNZKXSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3s)-3-ethylsulfonylbutyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)[C@@H](C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-SIKLNZKXSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• BWXFQDIMVOEZDG-OAQYLSRUSA-N 1-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3-propylurea Chemical compound CCCNC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 BWXFQDIMVOEZDG-OAQYLSRUSA-N 0.000 claims description 2
• NWHGDNXYTGVRTK-HXUWFJFHSA-N 1-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxopyrido[3,4-d]pyridazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]-3-propylurea Chemical compound CCCNC(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 NWHGDNXYTGVRTK-HXUWFJFHSA-N 0.000 claims description 2
• IJORANMSJMQSAY-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-ethylsulfonylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 IJORANMSJMQSAY-HXUWFJFHSA-N 0.000 claims description 2
• TWRLBTGKEAFDGO-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-ethylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 TWRLBTGKEAFDGO-LJQANCHMSA-N 0.000 claims description 2
• OVMCRVJLHVRHKE-HSZRJFAPSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-piperidin-1-ylsulfonylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCS(=O)(=O)N2CCCCC2)CCC1 OVMCRVJLHVRHKE-HSZRJFAPSA-N 0.000 claims description 2
• YXICCMIPIPEESR-AVKWCDSFSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylbutyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)C(C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-AVKWCDSFSA-N 0.000 claims description 2
• DLHRVVJGYOTOOA-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DLHRVVJGYOTOOA-OAQYLSRUSA-N 0.000 claims description 2
• JETJHTYYZHIZRJ-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JETJHTYYZHIZRJ-HXUWFJFHSA-N 0.000 claims description 2
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 2
• VTQRKNRZSDZHPN-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VTQRKNRZSDZHPN-HXUWFJFHSA-N 0.000 claims description 2
• YOJGSGWWEUHPBC-JOCHJYFZSA-N n-[4-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]butyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YOJGSGWWEUHPBC-JOCHJYFZSA-N 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
• 239000002904 solvent Substances 0.000 description 80
• 239000000543 intermediate Substances 0.000 description 69
• 239000000243 solution Substances 0.000 description 65
• -1 n- Hexyl Chemical group 0.000 description 56
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 48
• 238000002360 preparation method Methods 0.000 description 48
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 210000004027 cell Anatomy 0.000 description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• 239000005557 antagonist Substances 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
• 239000002253 acid Substances 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 239000007787 solid Substances 0.000 description 26
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
• 239000002585 base Substances 0.000 description 25
• 229960001340 histamine Drugs 0.000 description 25
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000000725 suspension Substances 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 238000004128 high performance liquid chromatography Methods 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• 230000008569 process Effects 0.000 description 16
• 235000017557 sodium bicarbonate Nutrition 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
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• 239000000843 powder Substances 0.000 description 12
• 102000005962 receptors Human genes 0.000 description 12
• 108020003175 receptors Proteins 0.000 description 12
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
• 239000000443 aerosol Substances 0.000 description 11
• 239000000872 buffer Substances 0.000 description 11
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
• 235000019341 magnesium sulphate Nutrition 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• 239000003755 preservative agent Substances 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 229910021529 ammonia Inorganic materials 0.000 description 10
• 238000003556 assay Methods 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 235000009518 sodium iodide Nutrition 0.000 description 10
• 239000012190 activator Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 239000012458 free base Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 8
• DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 8
• 229960003081 probenecid Drugs 0.000 description 8
• 239000012312 sodium hydride Substances 0.000 description 8
• 239000002562 thickening agent Substances 0.000 description 8
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 102000004384 Histamine H3 receptors Human genes 0.000 description 7
• 108090000981 Histamine H3 receptors Proteins 0.000 description 7
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• 239000003795 chemical substances by application Substances 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 239000000375 suspending agent Substances 0.000 description 7
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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• 239000000048 adrenergic agonist Substances 0.000 description 6
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• 239000008346 aqueous phase Substances 0.000 description 6
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000006184 cosolvent Substances 0.000 description 6
• 239000012043 crude product Substances 0.000 description 6
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• 239000012453 solvate Substances 0.000 description 6
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• MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 description 5
• 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 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
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• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 5
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
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• 238000010511 deprotection reaction Methods 0.000 description 5
• XTULMSXFIHGYFS-VLSRWLAYSA-N fluticasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4[C@@H](F)C[C@H]3[C@@H]2C[C@H]1C)C(=O)SCF)C(=O)C1=CC=CO1 XTULMSXFIHGYFS-VLSRWLAYSA-N 0.000 description 5
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