TWI354668B - Fused cyclic compounds - Google Patents

Info

Publication number

TWI354668B

TWI354668B TW096122999A TW96122999A TWI354668B TW I354668 B TWI354668 B TW I354668B TW 096122999 A TW096122999 A TW 096122999A TW 96122999 A TW96122999 A TW 96122999A TW I354668 B TWI354668 B TW I354668B

Authority

TW

Taiwan

Prior art keywords

group

compound

mixture

etoac

acid

Prior art date

2006-06-27

Links

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• 150000001923 cyclic compounds Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 293
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 135
• 150000003839 salts Chemical class 0.000 claims description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 359
• -1 oxime compound Chemical class 0.000 description 176
• 235000019439 ethyl acetate Nutrition 0.000 description 158
• 239000000203 mixture Substances 0.000 description 142
• 239000000243 solution Substances 0.000 description 100
• 239000002585 base Substances 0.000 description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
• 239000011541 reaction mixture Substances 0.000 description 71
• 238000006243 chemical reaction Methods 0.000 description 60
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 125000001424 substituent group Chemical group 0.000 description 45
• 235000011054 acetic acid Nutrition 0.000 description 44
• 238000004949 mass spectrometry Methods 0.000 description 43
• 125000003118 aryl group Chemical group 0.000 description 41
• 239000000284 extract Substances 0.000 description 40
• 125000000217 alkyl group Chemical group 0.000 description 39
• 239000003814 drug Substances 0.000 description 39
• 238000000034 method Methods 0.000 description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 37
• 230000002829 reductive effect Effects 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 239000007789 gas Substances 0.000 description 36
• 239000002904 solvent Substances 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
• 239000003795 chemical substances by application Substances 0.000 description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
• 238000005481 NMR spectroscopy Methods 0.000 description 31
• 125000003277 amino group Chemical group 0.000 description 31
• 125000000623 heterocyclic group Chemical group 0.000 description 31
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
• 125000003545 alkoxy group Chemical group 0.000 description 27
• 239000013078 crystal Substances 0.000 description 27
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 239000002253 acid Substances 0.000 description 25
• 229940079593 drug Drugs 0.000 description 25
• 239000012299 nitrogen atmosphere Substances 0.000 description 25
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 24
• 125000004429 atom Chemical group 0.000 description 24
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 24
• 239000008103 glucose Substances 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 23
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 23
• 229910052751 metal Inorganic materials 0.000 description 22
• 239000002184 metal Substances 0.000 description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 21
• 238000012360 testing method Methods 0.000 description 21
• NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 125000005843 halogen group Chemical group 0.000 description 20
• 238000002360 preparation method Methods 0.000 description 20
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 19
• 125000003396 thiol group Chemical group [H]S* 0.000 description 19
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
• 239000008280 blood Substances 0.000 description 18
• 206010012601 diabetes mellitus Diseases 0.000 description 18
• 210000004369 blood Anatomy 0.000 description 17
• 210000004027 cell Anatomy 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 16
• 239000003112 inhibitor Substances 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
• 239000012046 mixed solvent Substances 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• 235000011121 sodium hydroxide Nutrition 0.000 description 15
• 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 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 14
• 229910052739 hydrogen Inorganic materials 0.000 description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
• 229940124597 therapeutic agent Drugs 0.000 description 14
• 229930182558 Sterol Natural products 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 235000003702 sterols Nutrition 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• 239000000052 vinegar Substances 0.000 description 12
• 235000021419 vinegar Nutrition 0.000 description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 229910052786 argon Inorganic materials 0.000 description 11
• 125000004104 aryloxy group Chemical group 0.000 description 11
• 239000012230 colorless oil Substances 0.000 description 11
• 230000006870 function Effects 0.000 description 11
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 10
• 102100026148 Free fatty acid receptor 1 Human genes 0.000 description 10
• 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 description 10
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 230000032050 esterification Effects 0.000 description 10
• 238000005886 esterification reaction Methods 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• 125000001183 hydrocarbyl group Chemical group 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 10
• 229940044601 receptor agonist Drugs 0.000 description 10
• 239000000018 receptor agonist Substances 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 125000003282 alkyl amino group Chemical group 0.000 description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 125000003710 aryl alkyl group Chemical group 0.000 description 9
• 125000001769 aryl amino group Chemical group 0.000 description 9
• 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 description 9
• 229910052799 carbon Inorganic materials 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 125000004093 cyano group Chemical group *C#N 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 229910052707 ruthenium Inorganic materials 0.000 description 9
• 238000010898 silica gel chromatography Methods 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• 229940122199 Insulin secretagogue Drugs 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 239000001913 cellulose Substances 0.000 description 8
• 235000010980 cellulose Nutrition 0.000 description 8
• 229920002678 cellulose Polymers 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 238000007254 oxidation reaction Methods 0.000 description 8
• 150000002923 oximes Chemical class 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 150000003385 sodium Chemical class 0.000 description 8
• 239000012279 sodium borohydride Substances 0.000 description 8
• 229910000033 sodium borohydride Inorganic materials 0.000 description 8
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 238000005859 coupling reaction Methods 0.000 description 7
• 238000001514 detection method Methods 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 229930195733 hydrocarbon Natural products 0.000 description 7
• 238000006460 hydrolysis reaction Methods 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
• 239000000825 pharmaceutical preparation Substances 0.000 description 7
• 239000002689 soil Substances 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 229910021653 sulphate ion Inorganic materials 0.000 description 7
• 206010036790 Productive cough Diseases 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 239000000556 agonist Substances 0.000 description 6
• 238000005576 amination reaction Methods 0.000 description 6
• HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 6
• 150000004982 aromatic amines Chemical class 0.000 description 6
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 6
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• 239000004305 biphenyl Substances 0.000 description 6
• 235000010290 biphenyl Nutrition 0.000 description 6
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
• 238000007796 conventional method Methods 0.000 description 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 150000002430 hydrocarbons Chemical class 0.000 description 6
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
• 239000003446 ligand Substances 0.000 description 6
• 238000004519 manufacturing process Methods 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 230000003287 optical effect Effects 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 235000011181 potassium carbonates Nutrition 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 210000003802 sputum Anatomy 0.000 description 6
• 208000024794 sputum Diseases 0.000 description 6
• 150000003432 sterols Chemical class 0.000 description 6
• 235000000346 sugar Nutrition 0.000 description 6
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 5
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
• 241000282414 Homo sapiens Species 0.000 description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 5
• 229940100389 Sulfonylurea Drugs 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• 239000005864 Sulphur Substances 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 239000005557 antagonist Substances 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 239000011575 calcium Substances 0.000 description 5
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