TWI230609B - Combination therapy for the treatment of cancer - Google Patents

Info

Publication number

TWI230609B

TWI230609B TW091118425A TW91118425A TWI230609B TW I230609 B TWI230609 B TW I230609B TW 091118425 A TW091118425 A TW 091118425A TW 91118425 A TW91118425 A TW 91118425A TW I230609 B TWI230609 B TW I230609B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

hydrogen

aryl

carboxylic acid

Prior art date

2001-08-15

Links

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• Global Dossier
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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 87
• 201000011510 cancer Diseases 0.000 title claims description 47
• 238000011282 treatment Methods 0.000 title abstract description 40
• 238000002648 combination therapy Methods 0.000 title description 6
• 108010037462 Cyclooxygenase 2 Proteins 0.000 claims abstract description 25
• 229940124639 Selective inhibitor Drugs 0.000 claims abstract description 22
• 102000010907 Cyclooxygenase 2 Human genes 0.000 claims abstract 17
• -1 piperidine-1-ylmethyl Chemical group 0.000 claims description 403
• 150000001875 compounds Chemical class 0.000 claims description 255
• 229910052739 hydrogen Inorganic materials 0.000 claims description 200
• 239000001257 hydrogen Substances 0.000 claims description 199
• 125000000217 alkyl group Chemical group 0.000 claims description 195
• 125000003118 aryl group Chemical group 0.000 claims description 129
• 150000002431 hydrogen Chemical group 0.000 claims description 112
• 239000000203 mixture Substances 0.000 claims description 108
• 239000002253 acid Substances 0.000 claims description 104
• 125000003545 alkoxy group Chemical group 0.000 claims description 75
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 74
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
• 150000001412 amines Chemical group 0.000 claims description 71
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• 229910052799 carbon Inorganic materials 0.000 claims description 66
• 125000001072 heteroaryl group Chemical group 0.000 claims description 63
• 239000008194 pharmaceutical composition Substances 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical group 0.000 claims description 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 36
• 239000003814 drug Substances 0.000 claims description 33
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 26
• 239000003909 protein kinase inhibitor Substances 0.000 claims description 24
• 229940043355 kinase inhibitor Drugs 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• 125000004104 aryloxy group Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 108090000623 proteins and genes Proteins 0.000 claims description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 239000000460 chlorine Chemical group 0.000 claims description 12
• 239000011737 fluorine Chemical group 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
• QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 102000004169 proteins and genes Human genes 0.000 claims description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims description 5
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 230000001105 regulatory effect Effects 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 229930194542 Keto Natural products 0.000 claims description 3
• 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 3
• 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 3
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000001769 aryl amino group Chemical group 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000004385 trihaloalkyl group Chemical group 0.000 claims description 3
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=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
• 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 2
• 239000007983 Tris buffer Substances 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002837 carbocyclic group Chemical group 0.000 claims description 2
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
• 239000002532 enzyme inhibitor Substances 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 2
• 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 2
• 125000000468 ketone group Chemical group 0.000 claims description 2
• 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
• 125000004999 nitroaryl group Chemical group 0.000 claims description 2
• 239000003650 oxygenase inhibitor Substances 0.000 claims description 2
• 229960003495 thiamine Drugs 0.000 claims description 2
• 239000011721 thiamine Substances 0.000 claims description 2
• 150000004678 hydrides Chemical group 0.000 claims 10
• 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
• 125000006413 ring segment Chemical group 0.000 claims 9
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
• 125000005110 aryl thio group Chemical group 0.000 claims 6
• DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 claims 5
• 125000003367 polycyclic group Chemical group 0.000 claims 4
• 102200078752 rs201827340 Human genes 0.000 claims 4
• 102220241276 rs78592515 Human genes 0.000 claims 4
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims 3
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 3
• 125000002950 monocyclic group Chemical group 0.000 claims 3
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
• 125000004149 thio group Chemical group *S* 0.000 claims 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• LZNNMMKMGKFYLL-UHFFFAOYSA-N 2h-pyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=COC1 LZNNMMKMGKFYLL-UHFFFAOYSA-N 0.000 claims 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
• 125000001931 aliphatic group Chemical group 0.000 claims 2
• 125000002619 bicyclic group Chemical group 0.000 claims 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 2
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=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.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• QSLSQLYQCKEGMS-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QSLSQLYQCKEGMS-UHFFFAOYSA-N 0.000 claims 1
• MXDYXICPDYNAIF-UHFFFAOYSA-N 2-[6-(2-phenylethyl)-9H-fluoren-1-yl]-2-(trifluoromethyl)chromene-3-carboxylic acid Chemical compound C1(=CC=CC=C1)CCC=1C=C2C=3C=CC=C(C3CC2=CC1)C1(OC2=C(C=C1C(=O)O)C=CC=C2)C(F)(F)F MXDYXICPDYNAIF-UHFFFAOYSA-N 0.000 claims 1
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
• IPDYDSCYHHDDKL-UHFFFAOYSA-N 2-methoxy-2-(trifluoromethyl)chromene-3-carboxylic acid Chemical compound COC1(OC2=CC=CC=C2C=C1C(=O)O)C(F)(F)F IPDYDSCYHHDDKL-UHFFFAOYSA-N 0.000 claims 1
• VJBZDMNYBTXHOL-UHFFFAOYSA-N 2-methyl-2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C)OC2=C1 VJBZDMNYBTXHOL-UHFFFAOYSA-N 0.000 claims 1
• 125000004892 2-methylpropylamino group Chemical group CC(CN*)C 0.000 claims 1
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• RQQHLNVMWGHEFH-UHFFFAOYSA-N 2-tert-butyl-2-(trifluoromethyl)chromene-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(C)(C)C)(C(F)(F)F)OC2=C1 RQQHLNVMWGHEFH-UHFFFAOYSA-N 0.000 claims 1
• NIXQLMVKRBUSPF-UHFFFAOYSA-N 3-(dimethylamino)propanamide Chemical group CN(C)CCC(N)=O NIXQLMVKRBUSPF-UHFFFAOYSA-N 0.000 claims 1
• NNDYEFJEHIRCGB-UHFFFAOYSA-N 4-methyl-1h-1,3,5-triazine-2,4,6-triamine Chemical compound CC1(N)NC(N)=NC(N)=N1 NNDYEFJEHIRCGB-UHFFFAOYSA-N 0.000 claims 1
• MOYKDFAFGUWTQO-UHFFFAOYSA-N 6-benzylsulfonyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)CC1=CC=CC=C1 MOYKDFAFGUWTQO-UHFFFAOYSA-N 0.000 claims 1
• VEENGDJNDWZTOU-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 VEENGDJNDWZTOU-UHFFFAOYSA-N 0.000 claims 1
• FIGFIPYZSNLSOF-UHFFFAOYSA-N 6-chloro-7-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(CC)C(Cl)=C2 FIGFIPYZSNLSOF-UHFFFAOYSA-N 0.000 claims 1
• ZQRBVSGXWNRTHN-UHFFFAOYSA-N 6-chloro-7-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C)C(Cl)=C2 ZQRBVSGXWNRTHN-UHFFFAOYSA-N 0.000 claims 1
• QBEGCKDFGWDVKY-UHFFFAOYSA-N 6-chloro-8-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2CC QBEGCKDFGWDVKY-UHFFFAOYSA-N 0.000 claims 1
• NONBXOPYDWLZGR-UHFFFAOYSA-N 6-chloro-8-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C NONBXOPYDWLZGR-UHFFFAOYSA-N 0.000 claims 1
• WRXXEGPVSCGBRF-UHFFFAOYSA-N 6-methylsulfonyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)C)=CC=C21 WRXXEGPVSCGBRF-UHFFFAOYSA-N 0.000 claims 1
• OYURZHOTHWPVEX-UHFFFAOYSA-N 6-morpholin-4-ylsulfonyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)N1CCOCC1 OYURZHOTHWPVEX-UHFFFAOYSA-N 0.000 claims 1
• ZSRMQEBKMLQXMW-UHFFFAOYSA-N 7-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(CC)=CC=C21 ZSRMQEBKMLQXMW-UHFFFAOYSA-N 0.000 claims 1
• ABNPGORLVYQTCX-UHFFFAOYSA-N 7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 ABNPGORLVYQTCX-UHFFFAOYSA-N 0.000 claims 1
• MFIJXIQKTVUZEM-UHFFFAOYSA-N 7-tert-butyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=CC(C(C)(C)C)=CC=C21 MFIJXIQKTVUZEM-UHFFFAOYSA-N 0.000 claims 1
• UYSKIFTWJYWMQH-UHFFFAOYSA-N 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2h-chromene Chemical compound O1C(C(F)(F)F)C=CC2=C1C=C(C(C)(C)C)C(Cl)=C2 UYSKIFTWJYWMQH-UHFFFAOYSA-N 0.000 claims 1
• HWHWDSNSWIQJMF-UHFFFAOYSA-N 8-bromo-5-fluoro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1F HWHWDSNSWIQJMF-UHFFFAOYSA-N 0.000 claims 1
• ZIGWRQKLXXGWHR-UHFFFAOYSA-N 8-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ZIGWRQKLXXGWHR-UHFFFAOYSA-N 0.000 claims 1
• JPWVMGPBBNJBBV-UHFFFAOYSA-N 8-chloro-6-methoxy-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(OC)=CC(Cl)=C21 JPWVMGPBBNJBBV-UHFFFAOYSA-N 0.000 claims 1
• JTYJBUOQGLXJEC-UHFFFAOYSA-N 8-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC=CC=1C1=CC=CC=C1 JTYJBUOQGLXJEC-UHFFFAOYSA-N 0.000 claims 1
• VZKOADAYRNEHHF-UHFFFAOYSA-N C(C)(C)NC1=C(C=CC=C1)C=CC1=CC=CC=C1 Chemical compound C(C)(C)NC1=C(C=CC=C1)C=CC1=CC=CC=C1 VZKOADAYRNEHHF-UHFFFAOYSA-N 0.000 claims 1
• 101000855645 Camptotheca acuminata (S)-8-oxocitronellyl enol synthase CYC2 Proteins 0.000 claims 1
• 241001327708 Coriaria sarmentosa Species 0.000 claims 1
• 229910052693 Europium Inorganic materials 0.000 claims 1
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