TWI296926B - Interleukin-4 gene expression inhibitors - Google Patents

Info

Publication number

TWI296926B

TWI296926B TW092109279A TW92109279A TWI296926B TW I296926 B TWI296926 B TW I296926B TW 092109279 A TW092109279 A TW 092109279A TW 92109279 A TW92109279 A TW 92109279A TW I296926 B TWI296926 B TW I296926B

Authority

TW

Taiwan

Prior art keywords

indole

carboxylic acid

alkyl

ester

ylamino

Prior art date

2002-04-23

Links

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• Global Dossier
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• 108090000978 Interleukin-4 Proteins 0.000 title claims description 112
• 102000004388 Interleukin-4 Human genes 0.000 title claims description 110
• 229940028885 interleukin-4 Drugs 0.000 title claims description 106
• 230000014509 gene expression Effects 0.000 title description 33
• 239000003112 inhibitor Substances 0.000 title description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 325
• 125000000217 alkyl group Chemical group 0.000 claims description 260
• 150000001875 compounds Chemical class 0.000 claims description 228
• -1 schlossyl Chemical class 0.000 claims description 214
• 239000000203 mixture Substances 0.000 claims description 83
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 72
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 239000002253 acid Substances 0.000 claims description 56
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 49
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 45
• 239000007789 gas Substances 0.000 claims description 44
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 41
• 206010020751 Hypersensitivity Diseases 0.000 claims description 40
• 208000006673 asthma Diseases 0.000 claims description 39
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
• 230000002079 cooperative effect Effects 0.000 claims description 39
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• 108090000176 Interleukin-13 Proteins 0.000 claims description 34
• 102000003816 Interleukin-13 Human genes 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 33
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 229920001774 Perfluoroether Polymers 0.000 claims description 28
• 150000002148 esters Chemical class 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 24
• 235000019253 formic acid Nutrition 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 238000004519 manufacturing process Methods 0.000 claims description 20
• 206010039083 rhinitis Diseases 0.000 claims description 20
• 241000725643 Respiratory syncytial virus Species 0.000 claims description 18
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 17
• 230000007815 allergy Effects 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 16
• 239000000052 vinegar Substances 0.000 claims description 16
• 235000021419 vinegar Nutrition 0.000 claims description 16
• 201000004624 Dermatitis Diseases 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
• 150000004702 methyl esters Chemical class 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 14
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 13
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• QPZYGDVYAXCTLM-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 QPZYGDVYAXCTLM-UHFFFAOYSA-N 0.000 claims description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• 201000010105 allergic rhinitis Diseases 0.000 claims description 12
• 208000010668 atopic eczema Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 241000709661 Enterovirus Species 0.000 claims description 11
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 11
• 238000013518 transcription Methods 0.000 claims description 11
• 230000035897 transcription Effects 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000003944 tolyl group Chemical group 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 230000000172 allergic effect Effects 0.000 claims description 9
• 201000008937 atopic dermatitis Diseases 0.000 claims description 9
• 125000004494 ethyl ester group Chemical group 0.000 claims description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 8
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
• 210000002443 helper t lymphocyte Anatomy 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 239000011737 fluorine Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000004305 biphenyl Substances 0.000 claims description 6
• 235000010290 biphenyl Nutrition 0.000 claims description 6
• 125000006267 biphenyl group Chemical group 0.000 claims description 6
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 241000700605 Viruses Species 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 230000017307 interleukin-4 production Effects 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
• 230000000844 anti-bacterial effect Effects 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 150000002923 oximes Chemical class 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 206010012434 Dermatitis allergic Diseases 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 201000009961 allergic asthma Diseases 0.000 claims description 3
• 229910052786 argon Inorganic materials 0.000 claims description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
• PURLCWYUCGXQTN-UHFFFAOYSA-N ethyl 3-[propyl(pyridin-4-yl)amino]-1-benzothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC2=CC=CC=C2C=1N(CCC)C1=CC=NC=C1 PURLCWYUCGXQTN-UHFFFAOYSA-N 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• MHGXJMORBYVIRV-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-1-benzothiophene-2-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C=1SC2=CC=CC=C2C=1NC1=CC=NC=C1 MHGXJMORBYVIRV-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
• 150000003973 alkyl amines Chemical class 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
• QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 2
• 229940093499 ethyl acetate Drugs 0.000 claims 5
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 4
• IDOURVSIWIVCHB-UHFFFAOYSA-N C1=CC=C(C=C1)C=CNC2=C(NC3=C2C=CC(=C3)F)C(=O)O Chemical compound C1=CC=C(C=C1)C=CNC2=C(NC3=C2C=CC(=C3)F)C(=O)O IDOURVSIWIVCHB-UHFFFAOYSA-N 0.000 claims 3
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 3
• RKPLYODWXHBQQM-UHFFFAOYSA-N ethyl 3-(pyridin-4-ylamino)-1-benzothiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC2=CC=CC=C2C=1NC1=CC=NC=C1 RKPLYODWXHBQQM-UHFFFAOYSA-N 0.000 claims 3
• 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
• PVOZBLLCDWUBEP-FRKBZVPNSA-N methyl (1r,2r,4s)-4-[(2r,4s,5s,6s)-4-(dimethylamino)-5-[(2s,4s,5s,6s)-4-hydroxy-6-methyl-5-[(2r,6s)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10,12-pentahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=C(O)C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 PVOZBLLCDWUBEP-FRKBZVPNSA-N 0.000 claims 3
• ONUAUWZFFBDDGF-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-methyl-3-(pyridin-4-ylamino)indole-2-carboxylic acid Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2N(C)C(C(O)=O)=C1NC1=CC=NC=C1 ONUAUWZFFBDDGF-BTJKTKAUSA-N 0.000 claims 2
• AFNDYDOXMMANFI-UHFFFAOYSA-N 2-(diethylamino)ethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCN(CC)CCOC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 AFNDYDOXMMANFI-UHFFFAOYSA-N 0.000 claims 2
• FUGLXURADSSFEG-UHFFFAOYSA-N 3-(pyridin-4-ylamino)-6-(trifluoromethyl)-1-benzothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC2=CC(C(F)(F)F)=CC=C2C=1NC1=CC=NC=C1 FUGLXURADSSFEG-UHFFFAOYSA-N 0.000 claims 2
• FPKURCFQQJBDDK-UHFFFAOYSA-N C1=CC=C(C=C1)C=NC2=C(NC3=C2C=CC(=C3)Cl)C(=O)O Chemical compound C1=CC=C(C=C1)C=NC2=C(NC3=C2C=CC(=C3)Cl)C(=O)O FPKURCFQQJBDDK-UHFFFAOYSA-N 0.000 claims 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
• 230000002128 anti-rhinoviral effect Effects 0.000 claims 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• 229910052801 chlorine Inorganic materials 0.000 claims 2
• 229960002380 dibutyl phthalate Drugs 0.000 claims 2
• QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 claims 2
• QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical compound N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 claims 2
• CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims 2
• 150000003254 radicals Chemical class 0.000 claims 2
• PYSSHAMICMLSIJ-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound CCOC(=O)COC(=O)C=1NC2=CC=CC=C2C=1NC1=CC=NC=C1 PYSSHAMICMLSIJ-UHFFFAOYSA-N 0.000 claims 1
• MUEXUQOKWIFGKS-UHFFFAOYSA-N (n-(4-methylphenyl)sulfonylanilino)methyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C=CC=CC=1)COC(=O)C1=C(NC=2C=CN=CC=2)C2=CC=CC=C2N1 MUEXUQOKWIFGKS-UHFFFAOYSA-N 0.000 claims 1
• PDDWJLGBNYUCQO-UHFFFAOYSA-N 1,1-diethylguanidine Chemical compound CCN(CC)C(N)=N PDDWJLGBNYUCQO-UHFFFAOYSA-N 0.000 claims 1
• IJEZXLCQOMRKLE-UHFFFAOYSA-N 2-(didecylamino)acetic acid Chemical compound CCCCCCCCCCN(CC(O)=O)CCCCCCCCCC IJEZXLCQOMRKLE-UHFFFAOYSA-N 0.000 claims 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
• JMXACIJWOAVQRN-UHFFFAOYSA-N 2-oxo-2-pyrrolidin-1-ylacetic acid Chemical compound OC(=O)C(=O)N1CCCC1 JMXACIJWOAVQRN-UHFFFAOYSA-N 0.000 claims 1
• BSPIIAWBOGGPKD-UHFFFAOYSA-N 2-piperidin-1-ylethyl 3-(pyridin-4-ylamino)-1h-indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C(NC=2C=CN=CC=2)=C1C(=O)OCCN1CCCCC1 BSPIIAWBOGGPKD-UHFFFAOYSA-N 0.000 claims 1
• JQTRXJMLHLOVKX-UHFFFAOYSA-N 3-(benzenesulfonamido)-4,6-dichloro-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1NS(=O)(=O)C1=CC=CC=C1 JQTRXJMLHLOVKX-UHFFFAOYSA-N 0.000 claims 1
• XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 claims 1
• CNNZZZDURXSKEX-UHFFFAOYSA-N 4-fluoro-1-methyl-3-(pyridin-4-ylamino)indole-2-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=C(F)C=CC=C2N(C)C(C(O)=O)=C1NC1=CC=NC=C1 CNNZZZDURXSKEX-UHFFFAOYSA-N 0.000 claims 1
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
• GXMDNGBDAOUEEY-UHFFFAOYSA-N CCOC(=O)C1=C(C2=C(N1)C=C(C=C2Cl)Cl)NC(=CC3=CC=CC=C3)C4=CC=CC=C4 Chemical compound CCOC(=O)C1=C(C2=C(N1)C=C(C=C2Cl)Cl)NC(=CC3=CC=CC=C3)C4=CC=CC=C4 GXMDNGBDAOUEEY-UHFFFAOYSA-N 0.000 claims 1
• 206010027476 Metastases Diseases 0.000 claims 1
• HBVZRPAKZOLBPL-UHFFFAOYSA-N O-Acetylethanolamine Chemical compound CC(=O)OCCN HBVZRPAKZOLBPL-UHFFFAOYSA-N 0.000 claims 1
• BKLJXBLBVDKMLX-UHFFFAOYSA-N OC(=O)C(=O)n1ccc2ccccc12 Chemical compound OC(=O)C(=O)n1ccc2ccccc12 BKLJXBLBVDKMLX-UHFFFAOYSA-N 0.000 claims 1
• HGAPCFNXSLPISY-UHFFFAOYSA-N S1C=CC=C1.C(=O)OCC Chemical compound S1C=CC=C1.C(=O)OCC HGAPCFNXSLPISY-UHFFFAOYSA-N 0.000 claims 1
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
• 150000001356 alkyl thiols Chemical class 0.000 claims 1
• 125000004103 aminoalkyl group Chemical group 0.000 claims 1
• ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical compound C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 claims 1
• 230000003097 anti-respiratory effect Effects 0.000 claims 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
• 229910052797 bismuth Inorganic materials 0.000 claims 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
• 229960005286 carbaryl Drugs 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 239000000969 carrier Substances 0.000 claims 1
• 125000005265 dialkylamine group Chemical group 0.000 claims 1
• 229910003460 diamond Inorganic materials 0.000 claims 1
• 239000010432 diamond Substances 0.000 claims 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• QSCNLGHKALSYKF-UHFFFAOYSA-N ethoxymethanamine Chemical compound CCOCN QSCNLGHKALSYKF-UHFFFAOYSA-N 0.000 claims 1
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