KR101011848B1 - 모르폴린 화합물 - Google Patents

Info

Publication number

KR101011848B1

KR101011848B1 KR1020077007863A KR20077007863A KR101011848B1 KR 101011848 B1 KR101011848 B1 KR 101011848B1 KR 1020077007863 A KR1020077007863 A KR 1020077007863A KR 20077007863 A KR20077007863 A KR 20077007863A KR 101011848 B1 KR101011848 B1 KR 101011848B1

Authority

KR

South Korea

Prior art keywords

substituent

methyl

morpholin

ylthio

acetamide

Prior art date

2004-09-08

Links

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• -1 Morpholine compound Chemical class 0.000 title claims abstract description 388
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 516
• 125000001424 substituent group Chemical group 0.000 claims abstract description 312
• 150000003839 salts Chemical class 0.000 claims abstract description 75
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 62
• 125000003118 aryl group Chemical group 0.000 claims abstract description 47
• 239000012453 solvate Substances 0.000 claims abstract description 42
• 125000000732 arylene group Chemical group 0.000 claims abstract description 19
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 427
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 329
• 238000000034 method Methods 0.000 claims description 306
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 280
• 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 215
• 125000000217 alkyl group Chemical group 0.000 claims description 125
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
• 125000001072 heteroaryl group Chemical group 0.000 claims description 48
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 229910052717 sulfur Inorganic materials 0.000 claims description 39
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 38
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 38
• 125000004434 sulfur atom Chemical group 0.000 claims description 34
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 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 28
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 125000002950 monocyclic group Chemical group 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 16
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000004442 acylamino group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000006413 ring segment Chemical group 0.000 claims description 12
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
• 230000000172 allergic effect Effects 0.000 claims description 10
• 208000010668 atopic eczema Diseases 0.000 claims description 10
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 10
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 201000008937 atopic dermatitis Diseases 0.000 claims description 9
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 201000009890 sinusitis Diseases 0.000 claims description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 8
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 8
• 208000011231 Crohn disease Diseases 0.000 claims description 8
• 208000003926 Myelitis Diseases 0.000 claims description 8
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 8
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 8
• 201000010105 allergic rhinitis Diseases 0.000 claims description 8
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 150000004677 hydrates Chemical class 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 4
• 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 4
• VSYXRMYWASBQMG-KPMSDPLLSA-N N-[[(2S)-1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-2H-pyrimidin-2-yl]sulfanyl]acetamide Chemical compound C(C)(=O)NS[C@H]1N(C=CC=N1)CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl VSYXRMYWASBQMG-KPMSDPLLSA-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
• MBQDZFRXXOGGLZ-SFHVURJKSA-N N-[[(2S)-4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methyl]-4-cyclopentylsulfonylbutan-1-amine Chemical compound Fc1ccc(CN2CCO[C@@H](CNCCCCS(=O)(=O)C3CCCC3)C2)cc1Cl MBQDZFRXXOGGLZ-SFHVURJKSA-N 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 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 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• 150000003456 sulfonamides Chemical class 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
• BWZAEYLVCQTNFL-UWBLVGDVSA-N C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl)C1=NN=NN1 Chemical class C(C)(=O)NS[C@@H]1SC=C(N1CC1CN(CCO1)CC1=CC(=C(C=C1)Cl)Cl)C1=NN=NN1 BWZAEYLVCQTNFL-UWBLVGDVSA-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
• 238000009833 condensation Methods 0.000 claims description 3
• 230000005494 condensation Effects 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
• 235000012054 meals Nutrition 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• BPJJMLJROTXLFL-HNNXBMFYSA-N 2-[4-[[(2S)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylamino]butylsulfanyl]-1,3-thiazole-4-carboxamide Chemical compound NC(=O)c1csc(SCCCCNC[C@H]2CN(Cc3ccc(Cl)c(Cl)c3)CCO2)n1 BPJJMLJROTXLFL-HNNXBMFYSA-N 0.000 claims description 2
• MCYBOSMXXTXVNV-MBABXSBOSA-N N-[[(2S)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-4-(5-methyl-1,2,4-oxadiazol-3-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=NOC(=N1)C MCYBOSMXXTXVNV-MBABXSBOSA-N 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 6
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 3
• 150000003869 acetamides Chemical class 0.000 claims 1
• 102100024167 C-C chemokine receptor type 3 Human genes 0.000 abstract description 23
• 101710149862 C-C chemokine receptor type 3 Proteins 0.000 abstract description 23
• 239000003814 drug Substances 0.000 abstract description 12
• 102000019034 Chemokines Human genes 0.000 abstract description 8
• 108010012236 Chemokines Proteins 0.000 abstract description 8
• 208000026278 immune system disease Diseases 0.000 abstract description 7
• 208000027866 inflammatory disease Diseases 0.000 abstract description 5
• 238000003786 synthesis reaction Methods 0.000 description 459
• 230000015572 biosynthetic process Effects 0.000 description 457
• 239000000047 product Substances 0.000 description 324
• 239000007787 solid Substances 0.000 description 236
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 92
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
• 239000002904 solvent Substances 0.000 description 87
• 238000006243 chemical reaction Methods 0.000 description 63
• 239000012230 colorless oil Substances 0.000 description 63
• 239000000243 solution Substances 0.000 description 60
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 239000012046 mixed solvent Substances 0.000 description 48
• 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 46
• 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 41
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
• 239000003921 oil Substances 0.000 description 40
• 235000019198 oils Nutrition 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 239000002253 acid Substances 0.000 description 34
• CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 34
• 239000013078 crystal Substances 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 235000019270 ammonium chloride Nutrition 0.000 description 29
• 239000003480 eluent Substances 0.000 description 29
• 238000010898 silica gel chromatography Methods 0.000 description 29
• 239000000843 powder Substances 0.000 description 27
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
• 150000001408 amides Chemical class 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical compound NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 18
• 238000010992 reflux Methods 0.000 description 17
• 238000001816 cooling Methods 0.000 description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• 210000003979 eosinophil Anatomy 0.000 description 15
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
• 201000010099 disease Diseases 0.000 description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 13
• 125000004076 pyridyl group Chemical group 0.000 description 13
• 0 NC(NCC1OCCN*1)=O Chemical compound NC(NCC1OCCN*1)=O 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 125000000335 thiazolyl group Chemical group 0.000 description 12
• 238000000605 extraction Methods 0.000 description 11
• 125000002541 furyl group Chemical group 0.000 description 11
• 125000001544 thienyl group Chemical group 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 9
• 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
• 125000005605 benzo group Chemical group 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000001309 chloro group Chemical group Cl* 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 125000003373 pyrazinyl group Chemical group 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• 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
• AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 125000001153 fluoro group Chemical group F* 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
• 241000534944 Thia Species 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 230000002265 prevention Effects 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 125000002098 pyridazinyl group Chemical group 0.000 description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 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
• 239000011575 calcium Substances 0.000 description 6
• 229910052791 calcium Inorganic materials 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 238000010276 construction Methods 0.000 description 6
• 230000003834 intracellular effect Effects 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 125000003107 substituted aryl group Chemical group 0.000 description 6
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• 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
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• WHAXLDWKDSWXEO-UHFFFAOYSA-N diethyl 2-(6,7-dimethoxy-2-sulfanylidene-3h-quinazolin-4-yl)propanedioate Chemical compound COC1=C(OC)C=C2C(C(C(=O)OCC)C(=O)OCC)=NC(S)=NC2=C1 WHAXLDWKDSWXEO-UHFFFAOYSA-N 0.000 description 1
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• 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
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