TW200538127A - PGD2 receptor antagonists for the treatment of inflammatory diseases - Google Patents

Info

Publication number

TW200538127A

TW200538127A TW094111008A TW94111008A TW200538127A TW 200538127 A TW200538127 A TW 200538127A TW 094111008 A TW094111008 A TW 094111008A TW 94111008 A TW94111008 A TW 94111008A TW 200538127 A TW200538127 A TW 200538127A

Authority

TW

Taiwan

Prior art keywords

methyl

amino

substituted

group

phenyl

Prior art date

2004-04-07

Links

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• Global Dossier
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• 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 9
• 108050000258 Prostaglandin D receptors Proteins 0.000 title abstract description 21
• 102000009389 Prostaglandin D receptors Human genes 0.000 title description 20
• 239000002464 receptor antagonist Substances 0.000 title 1
• 229940044551 receptor antagonist Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 155
• -1 N-substituted nitrogen Chemical group 0.000 claims description 656
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 315
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 312
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 184
• 125000000217 alkyl group Chemical group 0.000 claims description 174
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 129
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 125
• 238000000034 method Methods 0.000 claims description 119
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 109
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 108
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
• 125000001188 haloalkyl group Chemical group 0.000 claims description 96
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 82
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 72
• 238000006243 chemical reaction Methods 0.000 claims description 67
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 65
• 239000002253 acid Substances 0.000 claims description 64
• QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 63
• 229910052799 carbon Inorganic materials 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 60
• 150000001412 amines Chemical group 0.000 claims description 54
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 45
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 44
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 41
• 125000002757 morpholinyl group Chemical group 0.000 claims description 39
• 150000001721 carbon Chemical group 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 33
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 230000002829 reductive effect Effects 0.000 claims description 28
• 235000019441 ethanol Nutrition 0.000 claims description 27
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 27
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 25
• 201000010099 disease Diseases 0.000 claims description 24
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 21
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
• 150000004820 halides Chemical class 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 19
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
• 125000005265 dialkylamine group Chemical group 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 18
• 239000007789 gas Substances 0.000 claims description 18
• 208000024891 symptom Diseases 0.000 claims description 18
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
• 125000002883 imidazolyl group Chemical group 0.000 claims description 15
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 15
• 238000006467 substitution reaction Methods 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004568 thiomorpholinyl group Chemical class 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 125000003003 spiro group Chemical group 0.000 claims description 12
• 239000007858 starting material Substances 0.000 claims description 12
• VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 claims description 11
• 150000003973 alkyl amines Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000006413 ring segment Chemical group 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 10
• 239000003153 chemical reaction reagent Substances 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
• 239000005711 Benzoic acid Substances 0.000 claims description 9
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 235000010233 benzoic acid Nutrition 0.000 claims description 9
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 150000004702 methyl esters Chemical class 0.000 claims description 9
• 235000019260 propionic acid Nutrition 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 9
• 235000021419 vinegar Nutrition 0.000 claims description 9
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 239000000052 vinegar Substances 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 7
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 7
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 7
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 7
• 125000005630 sialyl group Chemical group 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
• OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims description 6
• 230000003213 activating effect Effects 0.000 claims description 6
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
• DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 6
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
• 239000012279 sodium borohydride Substances 0.000 claims description 6
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000001118 alkylidene group Chemical group 0.000 claims description 5
• 150000001413 amino acids Chemical class 0.000 claims description 5
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• IGHXQNDUQCTKSH-UHFFFAOYSA-N methyl 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C(=O)OC IGHXQNDUQCTKSH-UHFFFAOYSA-N 0.000 claims description 5
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 5
• WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 4
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 4
• 201000009961 allergic asthma Diseases 0.000 claims description 4
• 230000009435 amidation Effects 0.000 claims description 4
• 238000007112 amidation reaction Methods 0.000 claims description 4
• 125000006242 amine protecting group Chemical group 0.000 claims description 4
• WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
• BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 4
• YKDCATRNPVJHMY-UHFFFAOYSA-N ethyl 2,2-dimethylbutanoate Chemical compound CCOC(=O)C(C)(C)CC YKDCATRNPVJHMY-UHFFFAOYSA-N 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical class O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000468 ketone group Chemical group 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• WZJLGICGNMAUFC-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-fluorene Chemical compound C12=CC=CC=C2CC2=C1CCCC2 WZJLGICGNMAUFC-UHFFFAOYSA-N 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 229930194542 Keto Natural products 0.000 claims description 3
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
• 125000006241 alcohol protecting group Chemical group 0.000 claims description 3
• 201000010105 allergic rhinitis Diseases 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 150000001805 chlorine compounds Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims description 3
• 125000001725 pyrenyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims description 3
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
• IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 2
• XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
• 206010061218 Inflammation Diseases 0.000 claims description 2
• CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 2
• 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 claims description 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
• 239000012190 activator Substances 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000002720 diazolyl group Chemical group 0.000 claims description 2
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 2
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
• 230000004054 inflammatory process Effects 0.000 claims description 2
• 239000012528 membrane Substances 0.000 claims description 2
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