TW200526628A - Quinazoline derivatives - Google Patents

Info

Publication number

TW200526628A

TW200526628A TW093128079A TW93128079A TW200526628A TW 200526628 A TW200526628 A TW 200526628A TW 093128079 A TW093128079 A TW 093128079A TW 93128079 A TW93128079 A TW 93128079A TW 200526628 A TW200526628 A TW 200526628A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

phenyl

amino

oxy

Prior art date

2003-09-16

Links

• Espacenet
• Global Dossier
• Discuss

• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract description 34
• 125000001424 substituent group Chemical group 0.000 claims abstract description 211
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 25
• 241001465754 Metazoa Species 0.000 claims abstract description 24
• 230000000694 effects Effects 0.000 claims abstract description 23
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract description 16
• 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract description 16
• 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 815
• -1 amidino, sulfamoyl Chemical group 0.000 claims description 696
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 392
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 264
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 258
• 125000003545 alkoxy group Chemical group 0.000 claims description 204
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 197
• 229910052757 nitrogen Inorganic materials 0.000 claims description 186
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 185
• 125000003282 alkyl amino group Chemical group 0.000 claims description 159
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 143
• 229910052739 hydrogen Inorganic materials 0.000 claims description 122
• 239000001257 hydrogen Substances 0.000 claims description 122
• 150000001875 compounds Chemical class 0.000 claims description 118
• 125000000623 heterocyclic group Chemical group 0.000 claims description 109
• 150000001412 amines Chemical class 0.000 claims description 105
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
• 125000005843 halogen group Chemical group 0.000 claims description 87
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 79
• 150000003839 salts Chemical class 0.000 claims description 76
• 235000019441 ethanol Nutrition 0.000 claims description 75
• 125000001153 fluoro group Chemical group F* 0.000 claims description 69
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 68
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 63
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
• 125000003342 alkenyl group Chemical group 0.000 claims description 57
• 125000000304 alkynyl group Chemical group 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 55
• 125000003277 amino group Chemical group 0.000 claims description 54
• 229910052799 carbon Inorganic materials 0.000 claims description 50
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 48
• 125000000468 ketone group Chemical group 0.000 claims description 48
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 47
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 39
• 125000004414 alkyl thio group Chemical group 0.000 claims description 37
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 33
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 30
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 28
• 150000001721 carbon Chemical group 0.000 claims description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 27
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 229930194542 Keto Natural products 0.000 claims description 24
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
• 108091000080 Phosphotransferase Proteins 0.000 claims description 23
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 23
• 102000020233 phosphotransferase Human genes 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 22
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
• 239000007789 gas Substances 0.000 claims description 22
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 21
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 21
• 125000000524 functional group Chemical group 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 19
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000006239 protecting group Chemical group 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 16
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 16
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 239000011593 sulfur Substances 0.000 claims description 15
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 150000002918 oxazolines Chemical class 0.000 claims description 13
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 12
• 239000003054 catalyst Substances 0.000 claims description 12
• DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 12
• 102000005133 Glutamate 5-kinase Human genes 0.000 claims description 11
• 108700023479 Glutamate 5-kinases Proteins 0.000 claims description 11
• 150000003973 alkyl amines Chemical class 0.000 claims description 11
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 241000282412 Homo Species 0.000 claims description 10
• ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical compound ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 150000003254 radicals Chemical class 0.000 claims description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 8
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 8
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 235000013336 milk Nutrition 0.000 claims description 7
• 239000008267 milk Substances 0.000 claims description 7
• 210000004080 milk Anatomy 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 150000007857 hydrazones Chemical class 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 5
• UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical compound OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 claims description 5
• BSABBBMNWQWLLU-UHFFFAOYSA-N lactaldehyde Chemical compound CC(O)C=O BSABBBMNWQWLLU-UHFFFAOYSA-N 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
• 210000002784 stomach Anatomy 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• OITHRYPVJIVVPG-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-4-amine Chemical compound NC1COC=N1 OITHRYPVJIVVPG-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 150000002431 hydrogen Chemical group 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000005323 thioketone group Chemical group 0.000 claims description 4
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
• IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims description 3
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
• 210000004369 blood Anatomy 0.000 claims description 3
• 239000008280 blood Substances 0.000 claims description 3
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 claims description 3
• 210000003296 saliva Anatomy 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 2
• MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000747 amidyl group Chemical group [H][N-]* 0.000 claims description 2
• 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 2
• 125000004175 fluorobenzyl group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims description 2
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
• 150000003246 quinazolines Chemical class 0.000 claims 21
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 2
• OQLKNTOKMBVBKV-UHFFFAOYSA-N hexamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 OQLKNTOKMBVBKV-UHFFFAOYSA-N 0.000 claims 2
• 229960001915 hexamidine Drugs 0.000 claims 2
• WDVIDPRACNGFPP-QWRGUYRKSA-N (2s)-2-[[(2s)-6-amino-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical class NCC(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O WDVIDPRACNGFPP-QWRGUYRKSA-N 0.000 claims 1
• SEHAXLDZJMQOCZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-oxidanylethane Chemical compound [O]CC(F)(F)F SEHAXLDZJMQOCZ-UHFFFAOYSA-N 0.000 claims 1
• KEVKXUZQHIMSCM-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanol Chemical compound CC(O)N1CCCC1 KEVKXUZQHIMSCM-UHFFFAOYSA-N 0.000 claims 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
• OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 claims 1
• OXIFSRBTDOYQIK-UHFFFAOYSA-N 2h-quinoxalin-1-amine Chemical compound C1=CC=C2N(N)CC=NC2=C1 OXIFSRBTDOYQIK-UHFFFAOYSA-N 0.000 claims 1
• AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 claims 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
• BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 claims 1
• MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 claims 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
• 239000004098 Tetracycline Substances 0.000 claims 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
• 125000001980 alanyl group Chemical group 0.000 claims 1
• 229910052786 argon Inorganic materials 0.000 claims 1
• 125000005518 carboxamido group Chemical group 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 238000005352 clarification Methods 0.000 claims 1
• 210000000078 claw Anatomy 0.000 claims 1
• 125000006006 difluoroethoxy group Chemical group 0.000 claims 1
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
• JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
• 125000005554 pyridyloxy group Chemical group 0.000 claims 1
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