IL113210A

IL113210A - 1H-Indole - 3 gliaxylamide sPLA2 inhibitors and preparations of pharmaceutical compounds containing them

1H-Indole - 3 gliaxylamide sPLA2 inhibitors and preparations of pharmaceutical compounds containing them

Info

Publication number: IL113210A
Authority: IL; Israel
Prior art keywords: group; methyl; indol; amino; alkyl
Prior art date: 1994-04-01

Application number

IL11321095A

Other languages

English (en)

Hebrew (he)

Other versions

IL113210A0 (en

Original Assignee

Lilly Co Eli

Priority date

1994-04-01

Filing date

1995-03-31

Publication date

2001-01-28

1995-03-31 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1995-06-29 Publication of IL113210A0 publication Critical patent/IL113210A0/xx

2001-01-28 Publication of IL113210A publication Critical patent/IL113210A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 10
AWMLDBKLOPNOAR-UHFFFAOYSA-N indole-3-glyoxylamide Natural products C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 title abstract description 7
239000003112 inhibitor Substances 0.000 title description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 68
239000001257 hydrogen Substances 0.000 claims abstract description 68
125000005647 linker group Chemical group 0.000 claims abstract description 54
125000001424 substituent group Chemical group 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 41
150000002431 hydrogen Chemical class 0.000 claims abstract description 41
230000002452 interceptive effect Effects 0.000 claims abstract description 32
125000005843 halogen group Chemical group 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
239000000651 prodrug Chemical class 0.000 claims abstract description 25
229940002612 prodrug Drugs 0.000 claims abstract description 25
125000004429 atom Chemical group 0.000 claims abstract description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
239000001301 oxygen Substances 0.000 claims abstract description 20
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052799 carbon Inorganic materials 0.000 claims abstract description 15
229910052717 sulfur Chemical group 0.000 claims abstract description 15
239000011593 sulfur Chemical group 0.000 claims abstract description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
239000012453 solvate Chemical class 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 4
-1 cy loalkenyl Chemical group 0.000 claims description 154
239000000203 mixture Substances 0.000 claims description 116
238000002360 preparation method Methods 0.000 claims description 109
150000001875 compounds Chemical class 0.000 claims description 98
239000002253 acid Substances 0.000 claims description 70
230000002378 acidificating effect Effects 0.000 claims description 53
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 36
239000004305 biphenyl Substances 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
102000005473 Secretory Phospholipases A2 Human genes 0.000 claims description 22
108010031873 Secretory Phospholipases A2 Proteins 0.000 claims description 22
235000010290 biphenyl Nutrition 0.000 claims description 18
229910006069 SO3H Inorganic materials 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 14
125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 claims description 14
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
125000002877 alkyl aryl group Chemical group 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 13
125000005425 toluyl group Chemical group 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 12
235000014113 dietary fatty acids Nutrition 0.000 claims description 11
229930195729 fatty acid Natural products 0.000 claims description 11
239000000194 fatty acid Substances 0.000 claims description 11
150000004665 fatty acids Chemical class 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
125000004438 haloalkoxy group Chemical group 0.000 claims description 9
230000001404 mediated effect Effects 0.000 claims description 9
150000003555 thioacetals Chemical class 0.000 claims description 9
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 9
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 7
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000004615 ingredient Substances 0.000 claims description 6
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000005593 norbornanyl group Chemical group 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims 3
241001024304 Mino Species 0.000 claims 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
BHLXTPHDSZUFHR-UHFFFAOYSA-N varespladib Chemical compound CCC1=C(C(=O)C(N)=O)C2=C(OCC(O)=O)C=CC=C2N1CC1=CC=CC=C1 BHLXTPHDSZUFHR-UHFFFAOYSA-N 0.000 claims 1
VJYDOJXJUCJUHL-UHFFFAOYSA-N varespladib methyl Chemical compound CCC1=C(C(=O)C(N)=O)C2=C(OCC(=O)OC)C=CC=C2N1CC1=CC=CC=C1 VJYDOJXJUCJUHL-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 312
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 168
235000019439 ethyl acetate Nutrition 0.000 description 139
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 127
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 84
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
238000004458 analytical method Methods 0.000 description 64
239000000741 silica gel Substances 0.000 description 56
229910002027 silica gel Inorganic materials 0.000 description 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
238000000034 method Methods 0.000 description 52
230000002829 reductive effect Effects 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 41
229910000104 sodium hydride Inorganic materials 0.000 description 39
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 38
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 33
239000002480 mineral oil Substances 0.000 description 29
235000010446 mineral oil Nutrition 0.000 description 29
239000004480 active ingredient Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
238000004587 chromatography analysis Methods 0.000 description 24
239000000047 product Substances 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
239000012267 brine Substances 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 18
AMANDCZTVNQSNB-UHFFFAOYSA-N glyoxamide Chemical group NC(=O)C=O AMANDCZTVNQSNB-UHFFFAOYSA-N 0.000 description 18
210000001519 tissue Anatomy 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 16
239000010410 layer Substances 0.000 description 16
239000003921 oil Substances 0.000 description 16
239000007787 solid Substances 0.000 description 15
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 14
238000009472 formulation Methods 0.000 description 13
239000000463 material Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
239000003826 tablet Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
150000002475 indoles Chemical class 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
229920002472 Starch Polymers 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 10
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000008107 starch Substances 0.000 description 10
235000019698 starch Nutrition 0.000 description 10
QFWNDWTXECQVOE-UHFFFAOYSA-N 4-methoxy-2-methyl-1h-indole Chemical compound COC1=CC=CC2=C1C=C(C)N2 QFWNDWTXECQVOE-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000004044 response Effects 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
231100000673 dose–response relationship Toxicity 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
238000011282 treatment Methods 0.000 description 8
238000003556 assay Methods 0.000 description 7
239000002585 base Substances 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 7
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 7
125000001041 indolyl group Chemical group 0.000 description 7
235000019359 magnesium stearate Nutrition 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229910015845 BBr3 Inorganic materials 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
229940114079 arachidonic acid Drugs 0.000 description 6
235000021342 arachidonic acid Nutrition 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000002198 insoluble material Substances 0.000 description 6
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
QNRDJVAPLVTDJJ-UHFFFAOYSA-N 2-ethyl-4-methoxy-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1OC QNRDJVAPLVTDJJ-UHFFFAOYSA-N 0.000 description 5
206010040070 Septic Shock Diseases 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
230000036303 septic shock Effects 0.000 description 5
RZZFTOJEHIRCRK-UHFFFAOYSA-N tert-butyl n-(3-methoxy-2-methylphenyl)carbamate Chemical compound COC1=CC=CC(NC(=O)OC(C)(C)C)=C1C RZZFTOJEHIRCRK-UHFFFAOYSA-N 0.000 description 5
SEXZHJJUKFXNDY-UHFFFAOYSA-N 1-(bromomethyl)-2-phenylbenzene Chemical group BrCC1=CC=CC=C1C1=CC=CC=C1 SEXZHJJUKFXNDY-UHFFFAOYSA-N 0.000 description 4
UNFSBZFKDUHXOX-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-2-ethylindol-4-ol Chemical compound CCC1=CC2=C(O)C=CC=C2N1CC1=CC=CC(Cl)=C1 UNFSBZFKDUHXOX-UHFFFAOYSA-N 0.000 description 4
XDYZMGCJQLDBQN-UHFFFAOYSA-N 1-benzyl-2-methylindol-4-ol Chemical compound CC1=CC2=C(O)C=CC=C2N1CC1=CC=CC=C1 XDYZMGCJQLDBQN-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 4
239000001768 carboxy methyl cellulose Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 4
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
FPDXBLLOWOIXJB-UHFFFAOYSA-N 1-[(2-phenylphenyl)methyl]-2-propylindol-4-ol Chemical compound CCCC1=CC2=C(O)C=CC=C2N1CC1=CC=CC=C1C1=CC=CC=C1 FPDXBLLOWOIXJB-UHFFFAOYSA-N 0.000 description 3
PRXUUGTYUMNKTR-UHFFFAOYSA-N 1-benzyl-2-cyclopropyl-4-methoxyindole Chemical compound C1CC1C1=CC=2C(OC)=CC=CC=2N1CC1=CC=CC=C1 PRXUUGTYUMNKTR-UHFFFAOYSA-N 0.000 description 3
LGCQIUWAFKRZMF-UHFFFAOYSA-N 1-benzyl-2-cyclopropylindol-4-ol Chemical compound C1CC1C1=CC=2C(O)=CC=CC=2N1CC1=CC=CC=C1 LGCQIUWAFKRZMF-UHFFFAOYSA-N 0.000 description 3
CICJSMPBNORTQN-UHFFFAOYSA-N 1-benzyl-2-ethyl-4-methoxyindole Chemical compound CCC1=CC2=C(OC)C=CC=C2N1CC1=CC=CC=C1 CICJSMPBNORTQN-UHFFFAOYSA-N 0.000 description 3
XATUTFYLKYJGBF-UHFFFAOYSA-N 1-benzyl-2-ethyl-5-methoxyindole Chemical compound CCC1=CC2=CC(OC)=CC=C2N1CC1=CC=CC=C1 XATUTFYLKYJGBF-UHFFFAOYSA-N 0.000 description 3
SUTVCLUFXXAFIP-UHFFFAOYSA-N 1-benzyl-4-methoxy-2-methylindole Chemical compound CC1=CC=2C(OC)=CC=CC=2N1CC1=CC=CC=C1 SUTVCLUFXXAFIP-UHFFFAOYSA-N 0.000 description 3
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