ES2396419T3 - Compuestos de morfolina para el tratamiento de inflamaciones - Google Patents

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Publication number

ES2396419T3

ES2396419T3 ES05783689T ES05783689T ES2396419T3 ES 2396419 T3 ES2396419 T3 ES 2396419T3 ES 05783689 T ES05783689 T ES 05783689T ES 05783689 T ES05783689 T ES 05783689T ES 2396419 T3 ES2396419 T3 ES 2396419T3

Authority

ES

Spain

Prior art keywords

substituent

methyl

morpholin

acetamide

ylthio

Prior art date

2004-09-08

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 238000011282 treatment Methods 0.000 title claims description 22
• 150000002780 morpholines Chemical class 0.000 title description 3
• 206010061218 Inflammation Diseases 0.000 title description 2
• 230000004054 inflammatory process Effects 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 520
• -1 nitro, amino Chemical group 0.000 claims abstract description 426
• 125000001424 substituent group Chemical group 0.000 claims abstract description 337
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 89
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 60
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 45
• 125000004429 atom Chemical group 0.000 claims abstract description 42
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 39
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 38
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 37
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 35
• 125000005843 halogen group Chemical group 0.000 claims abstract description 29
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 26
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 14
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 13
• 229910006074 SO2NH2 Inorganic materials 0.000 claims abstract description 12
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 11
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
• 125000002252 acyl group Chemical group 0.000 claims abstract description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 8
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 6
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
• 125000000464 thioxo group Chemical group S=* 0.000 claims abstract description 5
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 4
• 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims abstract description 4
• 229910006069 SO3H Inorganic materials 0.000 claims abstract description 4
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 4
• 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
• 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
• 238000000034 method Methods 0.000 claims description 382
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 266
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 236
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 173
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 154
• 150000003839 salts Chemical class 0.000 claims description 76
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 239000012453 solvate Substances 0.000 claims description 46
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 44
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 31
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 31
• 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 25
• 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 25
• 125000002947 alkylene group Chemical group 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 238000011321 prophylaxis Methods 0.000 claims description 18
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 125000004442 acylamino group Chemical group 0.000 claims description 13
• 230000000172 allergic effect Effects 0.000 claims description 13
• 208000006673 asthma Diseases 0.000 claims description 13
• 208000010668 atopic eczema Diseases 0.000 claims description 13
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 13
• 201000009890 sinusitis Diseases 0.000 claims description 13
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 12
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 12
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 12
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 12
• 208000003926 Myelitis Diseases 0.000 claims description 12
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 12
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 12
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 12
• 208000011231 Crohn disease Diseases 0.000 claims description 11
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 11
• 201000010105 allergic rhinitis Diseases 0.000 claims description 11
• 201000008937 atopic dermatitis Diseases 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000004450 alkenylene group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 9
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 9
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004419 alkynylene group Chemical group 0.000 claims description 7
• QBXNXHODSIQDRT-AWEZNQCLSA-N 2-[2-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(SCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 QBXNXHODSIQDRT-AWEZNQCLSA-N 0.000 claims description 6
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• SSOJXYMMWRJOKG-YSYXNDDBSA-N N-[[(2S)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-4-pyridin-4-yl-2H-1,3-thiazol-2-yl]sulfanyl]acetamide Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl)C1=CC=NC=C1 SSOJXYMMWRJOKG-YSYXNDDBSA-N 0.000 claims description 4
• NDZYPHLNJZSQJY-QNWVGRARSA-N 1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-[(1r,2s)-2-[[(3s)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexyl]urea Chemical compound CC1=C(C(=O)C)SC(NC(=O)N[C@H]2[C@@H](CCCC2)CN2C[C@H](CC=3C=CC(F)=CC=3)CCC2)=N1 NDZYPHLNJZSQJY-QNWVGRARSA-N 0.000 claims description 3
• QGONGVRPAFCFAI-SFHVURJKSA-N 2-[[4-(3-aminophenyl)-1,3-thiazol-2-yl]sulfanyl]-n-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]acetamide Chemical compound NC1=CC=CC(C=2N=C(SCC(=O)NC[C@@H]3OCCN(CC=4C=C(Cl)C(Cl)=CC=4)C3)SC=2)=C1 QGONGVRPAFCFAI-SFHVURJKSA-N 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• FRSWNSZEXNWJEF-AWEZNQCLSA-N N-[1-[[(2S)-4-[(3,4-difluorophenyl)methyl]morpholin-2-yl]methyl]-6-oxopyridazin-3-yl]sulfanylacetamide Chemical compound C(C)(=O)NSC1=NN(C(C=C1)=O)C[C@@H]1CN(CCO1)CC1=CC(=C(C=C1)F)F FRSWNSZEXNWJEF-AWEZNQCLSA-N 0.000 claims description 3
• RGSTTYKLYCVTOP-MBABXSBOSA-N N-[[(2S)-1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2H-[1,3]thiazolo[5,4-b]pyridin-2-yl]sulfanyl]acetamide Chemical compound C(C)(=O)NS[C@@H]1SC2=NC=CC=C2N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl RGSTTYKLYCVTOP-MBABXSBOSA-N 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• AXVSPJDWWCYULK-BIAFCPFJSA-N n-[[(2s)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-4-(3,4-dimethoxyphenyl)-2h-1,3-thiazol-2-yl]sulfanyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CS[C@@H](SNC(C)=O)N1CC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 AXVSPJDWWCYULK-BIAFCPFJSA-N 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
• 229910052760 oxygen Inorganic materials 0.000 claims 2
• 239000001301 oxygen Substances 0.000 claims 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 125000006413 ring segment Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract description 3
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 abstract description 2
• 125000000033 alkoxyamino group Chemical group 0.000 abstract 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 470
• 238000003786 synthesis reaction Methods 0.000 description 463
• 230000015572 biosynthetic process Effects 0.000 description 462
• 239000000047 product Substances 0.000 description 322
• 239000007787 solid Substances 0.000 description 234
• 238000005160 1H NMR spectroscopy Methods 0.000 description 233
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
• 239000000203 mixture Substances 0.000 description 93
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• 239000002904 solvent Substances 0.000 description 86
• 239000003480 eluent Substances 0.000 description 59
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 58
• 239000012230 colorless oil Substances 0.000 description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
• 239000011541 reaction mixture Substances 0.000 description 52
• 239000002253 acid Substances 0.000 description 51
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 239000012046 mixed solvent Substances 0.000 description 46
• 239000003921 oil Substances 0.000 description 44
• 235000019198 oils Nutrition 0.000 description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 43
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 239000013078 crystal Substances 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 31
• 235000019270 ammonium chloride Nutrition 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 29
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
• 239000000843 powder Substances 0.000 description 28
• 238000010898 silica gel chromatography Methods 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 17
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 17
• 238000010992 reflux Methods 0.000 description 16
• 229940086542 triethylamine Drugs 0.000 description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
• OJBBVTPPCDAKPT-XRIOVQLTSA-N [(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1CO[C@@H](CN)CN1CC1=CC=C(Cl)C(Cl)=C1 OJBBVTPPCDAKPT-XRIOVQLTSA-N 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• 235000017557 sodium bicarbonate Nutrition 0.000 description 14
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• 125000000335 thiazolyl group Chemical group 0.000 description 13
• 108010012236 Chemokines Proteins 0.000 description 12
• 102000019034 Chemokines Human genes 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 12
• 125000001544 thienyl group Chemical group 0.000 description 12
• 238000010276 construction Methods 0.000 description 11
• 125000002541 furyl group Chemical group 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 125000004076 pyridyl group Chemical group 0.000 description 11
• 150000001721 carbon Chemical group 0.000 description 10
• MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 102000009410 Chemokine receptor Human genes 0.000 description 9
• 108050000299 Chemokine receptor Proteins 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 125000001309 chloro group Chemical group Cl* 0.000 description 9
• 125000006286 dichlorobenzyl group Chemical group 0.000 description 9
• 125000003373 pyrazinyl group Chemical group 0.000 description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 8
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 description 8
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• UANWWXRZQGYWSR-JTQLQIEISA-N [(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methanamine Chemical compound C1CO[C@@H](CN)CN1CC1=CC=C(Cl)C(Cl)=C1 UANWWXRZQGYWSR-JTQLQIEISA-N 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• 125000002098 pyridazinyl group Chemical group 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 description 7
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 7
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• 125000005605 benzo group Chemical group 0.000 description 7
• 210000003979 eosinophil Anatomy 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 229910052739 hydrogen Inorganic materials 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
• WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 6
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• 238000005481 NMR spectroscopy Methods 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• 125000002785 azepinyl group Chemical group 0.000 description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 210000003692 ilium Anatomy 0.000 description 5
• 208000026278 immune system disease Diseases 0.000 description 5
• 125000001786 isothiazolyl group Chemical group 0.000 description 5
• 125000002971 oxazolyl group Chemical group 0.000 description 5
• 239000000825 pharmaceutical preparation Substances 0.000 description 5
• 229940127557 pharmaceutical product Drugs 0.000 description 5
• 125000003226 pyrazolyl group Chemical group 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 150000003512 tertiary amines Chemical class 0.000 description 5
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 5
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 4
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 4
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• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
• 125000005959 diazepanyl group Chemical group 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• MWWKOKHXOIXUOO-UHFFFAOYSA-N diethyl 2-(2-chloro-6,7-dimethoxyquinazolin-4-yl)propanedioate Chemical compound COC1=C(OC)C=C2C(C(C(=O)OCC)C(=O)OCC)=NC(Cl)=NC2=C1 MWWKOKHXOIXUOO-UHFFFAOYSA-N 0.000 description 1
• ZXEOXAINQLLLAK-UHFFFAOYSA-N diethyl 2-(2-chloropyrimidin-4-yl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=NC(Cl)=N1 ZXEOXAINQLLLAK-UHFFFAOYSA-N 0.000 description 1
• MBQAVYKJEGDMRP-UHFFFAOYSA-N diethyl 2-(2-sulfanylidene-1h-pyrimidin-6-yl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=NC(S)=N1 MBQAVYKJEGDMRP-UHFFFAOYSA-N 0.000 description 1
• DKHRRFGNQNIHDZ-IXXGTQFESA-N diethyl 2-[(2S)-2-acetamidosulfanyl-1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2H-pyrimidin-4-yl]propanedioate Chemical compound C(C)(=O)NS[C@H]1N(C=CC(=N1)C(C(=O)OCC)C(=O)OCC)CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl DKHRRFGNQNIHDZ-IXXGTQFESA-N 0.000 description 1
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 230000006806 disease prevention Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• CLPHAYNBNTVRDI-UHFFFAOYSA-N ditert-butyl propanedioate Chemical compound CC(C)(C)OC(=O)CC(=O)OC(C)(C)C CLPHAYNBNTVRDI-UHFFFAOYSA-N 0.000 description 1
• 239000012990 dithiocarbamate Substances 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
• GYYAQPORJUQZSS-MRNPHLECSA-N ethyl (2S)-2-acetamidosulfanyl-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-5-methyl-2H-1,3-thiazole-4-carboxylate Chemical compound C(C)(=O)NS[C@@H]1SC(=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl)C(=O)OCC)C GYYAQPORJUQZSS-MRNPHLECSA-N 0.000 description 1
• MWCWPPHTEINEQC-UHFFFAOYSA-N ethyl 1-(2-sulfanylidene-3h-1,3-thiazol-4-yl)cyclopropane-1-carboxylate Chemical compound C=1SC(S)=NC=1C1(C(=O)OCC)CC1 MWCWPPHTEINEQC-UHFFFAOYSA-N 0.000 description 1
• ZIXKPHHHPPZJFK-UHFFFAOYSA-N ethyl 2-(2-sulfanylidene-3h-1,3-thiazol-4-yl)acetate Chemical compound CCOC(=O)CC1=CSC(S)=N1 ZIXKPHHHPPZJFK-UHFFFAOYSA-N 0.000 description 1
• CUKOBNYGRGOBRH-UHFFFAOYSA-N ethyl 2-(6,7-dimethoxy-2-sulfanylidene-3h-quinazolin-4-yl)acetate Chemical compound COC1=C(OC)C=C2C(CC(=O)OCC)=NC(S)=NC2=C1 CUKOBNYGRGOBRH-UHFFFAOYSA-N 0.000 description 1
• VOBFWIFMTHXMBN-UHFFFAOYSA-N ethyl 2-(6,7-dimethoxyquinazolin-4-yl)acetate Chemical compound C(C)OC(=O)CC1=NC=NC2=CC(=C(C=C12)OC)OC VOBFWIFMTHXMBN-UHFFFAOYSA-N 0.000 description 1
• VBZCBEOUVVEXRV-LFABVHOISA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl)CC(=O)OCC VBZCBEOUVVEXRV-LFABVHOISA-N 0.000 description 1
• JCWSHQKONYNWNX-LFABVHOISA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(3-chloro-2-fluorophenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=C(C(=CC=C1)Cl)F)CC(=O)OCC JCWSHQKONYNWNX-LFABVHOISA-N 0.000 description 1
• RSRXAWXUJWSFPM-LFABVHOISA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)F)Cl)CC(=O)OCC RSRXAWXUJWSFPM-LFABVHOISA-N 0.000 description 1
• BXKGVOLKTFNFOO-BPARTEKVSA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(3-chloro-4-methylphenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)C)Cl)CC(=O)OCC BXKGVOLKTFNFOO-BPARTEKVSA-N 0.000 description 1
• WUOGLAAEEVSADA-QWAKEFERSA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(3-chlorophenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=CC=C1)Cl)CC(=O)OCC WUOGLAAEEVSADA-QWAKEFERSA-N 0.000 description 1
• TWFXZEXRCFMZSN-LFABVHOISA-N ethyl 2-[(2S)-2-acetamidosulfanyl-3-[[4-[(4-chloro-3-fluorophenyl)methyl]morpholin-2-yl]methyl]-2H-1,3-thiazol-4-yl]acetate Chemical compound C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)F)CC(=O)OCC TWFXZEXRCFMZSN-LFABVHOISA-N 0.000 description 1
• ZTDWJKYVAGYQMK-SFHVURJKSA-N ethyl 2-[2-[2-[[(2s)-4-[(4-chlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(SCC(=O)NC[C@@H]2OCCN(CC=3C=CC(Cl)=CC=3)C2)=N1 ZTDWJKYVAGYQMK-SFHVURJKSA-N 0.000 description 1
• UCAMRRCHHFAETO-SFHVURJKSA-N ethyl 2-[2-[2-[[(2s)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(SCC(=O)NC[C@@H]2OCCN(CC=3C=CC(F)=CC=3)C2)=N1 UCAMRRCHHFAETO-SFHVURJKSA-N 0.000 description 1
• XUPLCGBWPLRIFM-NSHDSACASA-N ethyl 2-[2-[2-[[(2s)-morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazol-4-yl]acetate Chemical compound CCOC(=O)CC1=CSC(SCC(=O)NC[C@H]2OCCNC2)=N1 XUPLCGBWPLRIFM-NSHDSACASA-N 0.000 description 1
• HLXBHPWLBWSQES-AWEZNQCLSA-N ethyl 2-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(SCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 HLXBHPWLBWSQES-AWEZNQCLSA-N 0.000 description 1
• MFQFGLVRWOLQLF-IBGZPJMESA-N ethyl 2-[4-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanylphenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1SCC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 MFQFGLVRWOLQLF-IBGZPJMESA-N 0.000 description 1
• JNMGULDEOSUUNM-INIZCTEOSA-N ethyl 2-[4-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-4-oxobutyl]sulfanyl-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(SCCCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 JNMGULDEOSUUNM-INIZCTEOSA-N 0.000 description 1
• OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 1
• RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
• UDDSDBJYAMHCCW-UHFFFAOYSA-N ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1C(F)(F)F UDDSDBJYAMHCCW-UHFFFAOYSA-N 0.000 description 1
• WTGNEFWADGCDBI-UHFFFAOYSA-N ethyl 2-sulfanylidene-3h-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(=S)N1 WTGNEFWADGCDBI-UHFFFAOYSA-N 0.000 description 1
• CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
• SIOIQIWIQSMQAG-UHFFFAOYSA-N ethyl 3-bromo-2-oxobutanoate Chemical compound CCOC(=O)C(=O)C(C)Br SIOIQIWIQSMQAG-UHFFFAOYSA-N 0.000 description 1
• VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
• OHKNSXMQSNDXAI-UHFFFAOYSA-N ethyl 4-methyl-2-sulfanylidene-3h-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(=S)NC=1C OHKNSXMQSNDXAI-UHFFFAOYSA-N 0.000 description 1
• FQFSHLBWRUOCPX-UHFFFAOYSA-N ethyl 4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CNC(=S)NC1=O FQFSHLBWRUOCPX-UHFFFAOYSA-N 0.000 description 1
• GUYZRQOTADGHII-UHFFFAOYSA-N ethyl 5-(2-bromoacetyl)-1,2-oxazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C(=O)CBr)ON=1 GUYZRQOTADGHII-UHFFFAOYSA-N 0.000 description 1
• NBXLGGSVNYQKPR-UHFFFAOYSA-N ethyl 5-(2-sulfanylidene-3h-1,3-thiazol-4-yl)-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OCC)C=C1C1=CSC(S)=N1 NBXLGGSVNYQKPR-UHFFFAOYSA-N 0.000 description 1
• PYGSXBQOZFWTPW-KRWDZBQOSA-N ethyl 5-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(SCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 PYGSXBQOZFWTPW-KRWDZBQOSA-N 0.000 description 1
• MVJPVDSRSXLJNQ-UHFFFAOYSA-N ethyl 5-bromopyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=C(Br)C=N1 MVJPVDSRSXLJNQ-UHFFFAOYSA-N 0.000 description 1
• PCPIANOJERKFJI-UHFFFAOYSA-N ethyl 5-bromopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(Br)=C1 PCPIANOJERKFJI-UHFFFAOYSA-N 0.000 description 1
• VQDMWIFJQSRHOI-UHFFFAOYSA-N ethyl 5-methyl-2-sulfanylidene-3h-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=C(S)SC=1C VQDMWIFJQSRHOI-UHFFFAOYSA-N 0.000 description 1
• MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
• FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 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 description 1
• 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000009610 hypersensitivity Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000005835 indanylene group Chemical group 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 210000004969 inflammatory cell Anatomy 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000005969 isothiazolinyl group Chemical group 0.000 description 1
• 125000003971 isoxazolinyl group Chemical group 0.000 description 1
• 210000001821 langerhans cell Anatomy 0.000 description 1
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 210000004698 lymphocyte Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
• PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
• DODCBMODXGJOKD-RGMNGODLSA-N methyl (2s)-2-amino-4-methylpentanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC(C)C DODCBMODXGJOKD-RGMNGODLSA-N 0.000 description 1
• ULSSGHADTSRELG-UHFFFAOYSA-N methyl 2-(3-bromophenyl)acetate Chemical compound COC(=O)CC1=CC=CC(Br)=C1 ULSSGHADTSRELG-UHFFFAOYSA-N 0.000 description 1
• MJBIEVZJGGUYSN-UHFFFAOYSA-N methyl 2-(4-bromophenoxy)-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC1=CC=C(Br)C=C1 MJBIEVZJGGUYSN-UHFFFAOYSA-N 0.000 description 1
• FCNYOGAKDMMTDC-UHFFFAOYSA-N methyl 2-(6-sulfanylidene-1h-pyridazin-3-yl)acetate Chemical compound COC(=O)CC1=CC=C(S)N=N1 FCNYOGAKDMMTDC-UHFFFAOYSA-N 0.000 description 1
• OOAUMMBSRQCJDW-HNNXBMFYSA-N methyl 2-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanylpyrimidine-5-carboxylate Chemical compound N1=CC(C(=O)OC)=CN=C1SCC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 OOAUMMBSRQCJDW-HNNXBMFYSA-N 0.000 description 1
• JVIGIBRXMCACMR-UHFFFAOYSA-N methyl 2-benzylsulfanyl-4-methylpyrimidine-5-carboxylate Chemical compound N1=C(C)C(C(=O)OC)=CN=C1SCC1=CC=CC=C1 JVIGIBRXMCACMR-UHFFFAOYSA-N 0.000 description 1
• PDSDTSSLFDCAIS-UHFFFAOYSA-N methyl 2-benzylsulfanylpyrimidine-5-carboxylate Chemical compound N1=CC(C(=O)OC)=CN=C1SCC1=CC=CC=C1 PDSDTSSLFDCAIS-UHFFFAOYSA-N 0.000 description 1
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
• ZSJJSQBUGDSCKW-UHFFFAOYSA-N methyl 2-methyl-2-(2-sulfanylidene-3h-1,3-thiazol-4-yl)propanoate Chemical compound COC(=O)C(C)(C)C1=CSC(S)=N1 ZSJJSQBUGDSCKW-UHFFFAOYSA-N 0.000 description 1
• QBKLHSXBHUMDII-KRWDZBQOSA-N methyl 3-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC(SCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 QBKLHSXBHUMDII-KRWDZBQOSA-N 0.000 description 1
• LFGRGJFMWACNLR-UHFFFAOYSA-N methyl 4-(2-chloroacetyl)benzoate Chemical compound COC(=O)C1=CC=C(C(=O)CCl)C=C1 LFGRGJFMWACNLR-UHFFFAOYSA-N 0.000 description 1
• PAVMVWRHWQJLKG-IBGZPJMESA-N methyl 4-[2-[2-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]-2-oxoethyl]sulfanyl-1,3-thiazol-4-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CSC(SCC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 PAVMVWRHWQJLKG-IBGZPJMESA-N 0.000 description 1
• ZZUYIRISBMWFMV-UHFFFAOYSA-N methyl 4-chlorobutanoate Chemical compound COC(=O)CCCCl ZZUYIRISBMWFMV-UHFFFAOYSA-N 0.000 description 1
• FBPIDMAELBIRLE-UHFFFAOYSA-N methyl 5-bromofuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(Br)O1 FBPIDMAELBIRLE-UHFFFAOYSA-N 0.000 description 1
• CSJHGVIKEOYMML-UHFFFAOYSA-N methyl 6-bromo-2-oxochromene-3-carboxylate Chemical compound BrC1=CC=C2OC(=O)C(C(=O)OC)=CC2=C1 CSJHGVIKEOYMML-UHFFFAOYSA-N 0.000 description 1
• JEUBRLPXJZOGPX-UHFFFAOYSA-N methyl 6-bromonaphthalene-2-carboxylate Chemical compound C1=C(Br)C=CC2=CC(C(=O)OC)=CC=C21 JEUBRLPXJZOGPX-UHFFFAOYSA-N 0.000 description 1
• BXGDVRAQHTXSEV-UHFFFAOYSA-N methyl 7-bromo-1-methyl-2,3-dihydro-1-benzazepine-4-carboxylate Chemical compound CN1CCC(C(=O)OC)=CC2=CC(Br)=CC=C21 BXGDVRAQHTXSEV-UHFFFAOYSA-N 0.000 description 1
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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