KR20040093488A - 화합물 - Google Patents

Info

Publication number

KR20040093488A

KR20040093488A KR10-2004-7015398A KR20047015398A KR20040093488A KR 20040093488 A KR20040093488 A KR 20040093488A KR 20047015398 A KR20047015398 A KR 20047015398A KR 20040093488 A KR20040093488 A KR 20040093488A

Authority

KR

South Korea

Prior art keywords

methyl

compound

formula

morpholin

urea

Prior art date

2002-03-28

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.)

Withdrawn

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 383
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 92
• 239000001257 hydrogen Substances 0.000 claims abstract description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 43
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 41
• 239000012453 solvate Substances 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 125000003118 aryl group Chemical group 0.000 claims abstract description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
• -1 3-formamido-1,2,4-triazol-5-yl Chemical group 0.000 claims description 418
• 238000000034 method Methods 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 208000006673 asthma Diseases 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• 239000004202 carbamide Substances 0.000 claims description 14
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 13
• 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 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 208000027866 inflammatory disease Diseases 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 9
• HIMWHLGWENNHOO-RUINGEJQSA-N (4-nitrophenyl) n-[[(2s)-4-[1-(3,4-difluorophenyl)ethyl]morpholin-2-yl]methyl]carbamate Chemical compound C([C@@H]1OCCN(C1)C(C)C=1C=C(F)C(F)=CC=1)NC(=O)OC1=CC=C([N+]([O-])=O)C=C1 HIMWHLGWENNHOO-RUINGEJQSA-N 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 206010039083 rhinitis Diseases 0.000 claims description 8
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 229920005989 resin Polymers 0.000 claims description 7
• 239000011347 resin Substances 0.000 claims description 7
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 4
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• DJVBYKUXZPCRCL-INIZCTEOSA-N (4-nitrophenyl) n-[[(2s)-4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methyl]carbamate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(F)=CC=2)C1 DJVBYKUXZPCRCL-INIZCTEOSA-N 0.000 claims description 3
• XLUKYSBCGPFVOU-UHFFFAOYSA-N 1-[(5-amino-1-phenylpyrazol-4-yl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=NN(C=2C=CC=CC=2)C(N)=C1CNC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 XLUKYSBCGPFVOU-UHFFFAOYSA-N 0.000 claims description 3
• JZBGNRGEOVQVEE-LBPRGKRZSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(2-methyltetrazol-5-yl)methyl]urea Chemical compound CN1N=NC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 JZBGNRGEOVQVEE-LBPRGKRZSA-N 0.000 claims description 3
• SOANXCFVMUFQHE-AWEZNQCLSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(4-methyl-1,3-thiazol-2-yl)methyl]urea Chemical compound CC1=CSC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 SOANXCFVMUFQHE-AWEZNQCLSA-N 0.000 claims description 3
• JLJGCRRYIYNEQJ-FQEVSTJZSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methyl]urea Chemical compound C1=CC(OC)=CC=C1C1=NOC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 JLJGCRRYIYNEQJ-FQEVSTJZSA-N 0.000 claims description 3
• KMAFRTKBDGSAJJ-IBGZPJMESA-N 1-[[3-(4-chlorophenyl)-1,2-oxazol-5-yl]methyl]-3-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1C1=NOC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 KMAFRTKBDGSAJJ-IBGZPJMESA-N 0.000 claims description 3
• CHFLRXHBQCODJY-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1,3-thiazol-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2SC=CN=2)OCC1 CHFLRXHBQCODJY-UHFFFAOYSA-N 0.000 claims description 3
• LJQCWQGMVJGSKQ-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1h-indol-4-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=3C=CNC=3C=CC=2)OCC1 LJQCWQGMVJGSKQ-UHFFFAOYSA-N 0.000 claims description 3
• YSSDLSCDXACWQT-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1h-indol-5-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=C3C=CNC3=CC=2)OCC1 YSSDLSCDXACWQT-UHFFFAOYSA-N 0.000 claims description 3
• PHMMAHLAVAGBGI-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C3=CC=CN=C3NC=2)OCC1 PHMMAHLAVAGBGI-UHFFFAOYSA-N 0.000 claims description 3
• YESMWHHSKLCUDO-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(2-thiophen-2-ylethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCCC=2SC=CC=2)OCC1 YESMWHHSKLCUDO-UHFFFAOYSA-N 0.000 claims description 3
• UBRNPKULFLNKTN-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(furan-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2OC=CC=2)OCC1 UBRNPKULFLNKTN-UHFFFAOYSA-N 0.000 claims description 3
• JOAMKEZJIZMCCP-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(pyridin-3-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=NC=CC=2)OCC1 JOAMKEZJIZMCCP-UHFFFAOYSA-N 0.000 claims description 3
• PMMVLXWWCMYNLR-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(thiophen-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2SC=CC=2)OCC1 PMMVLXWWCMYNLR-UHFFFAOYSA-N 0.000 claims description 3
• ZXAYMAJLQPFCEI-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(2-methyl-1,3-thiazol-4-yl)methyl]urea Chemical compound S1C(C)=NC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 ZXAYMAJLQPFCEI-UHFFFAOYSA-N 0.000 claims description 3
• JZBGNRGEOVQVEE-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(2-methyltetrazol-5-yl)methyl]urea Chemical compound CN1N=NC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 JZBGNRGEOVQVEE-UHFFFAOYSA-N 0.000 claims description 3
• ZALONBKTWCFUDD-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(3-methoxy-1,2-thiazol-5-yl)methyl]urea Chemical compound S1N=C(OC)C=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 ZALONBKTWCFUDD-UHFFFAOYSA-N 0.000 claims description 3
• SOANXCFVMUFQHE-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(4-methyl-1,3-thiazol-2-yl)methyl]urea Chemical compound CC1=CSC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 SOANXCFVMUFQHE-UHFFFAOYSA-N 0.000 claims description 3
• KKDYVYFNQWWRRG-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(5-methyl-1,2-oxazol-3-yl)methyl]urea Chemical compound O1C(C)=CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 KKDYVYFNQWWRRG-UHFFFAOYSA-N 0.000 claims description 3
• PONVDQFSFUCTIN-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(6-methoxypyridin-3-yl)methyl]urea Chemical compound C1=NC(OC)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 PONVDQFSFUCTIN-UHFFFAOYSA-N 0.000 claims description 3
• WQNPBIUZGHSLPX-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[5-[(dimethylamino)methyl]furan-2-yl]methyl]urea Chemical compound O1C(CN(C)C)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 WQNPBIUZGHSLPX-UHFFFAOYSA-N 0.000 claims description 3
• NYLJYXFMJQIKII-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[5-[(dimethylamino)methyl]thiophen-2-yl]methyl]urea Chemical compound S1C(CN(C)C)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 NYLJYXFMJQIKII-UHFFFAOYSA-N 0.000 claims description 3
• VKJDDBJDNJOXOP-UHFFFAOYSA-N 2-(5-methyl-1,3,4-oxadiazol-2-yl)ethanamine Chemical compound CC1=NN=C(CCN)O1 VKJDDBJDNJOXOP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• SHWHZSUZZGMZID-UHFFFAOYSA-N 5-(aminomethyl)-n-methyl-1,3,4-oxadiazole-2-carboxamide;hydrochloride Chemical compound Cl.CNC(=O)C1=NN=C(CN)O1 SHWHZSUZZGMZID-UHFFFAOYSA-N 0.000 claims description 3
• FWJJBJSRDWAPHW-UHFFFAOYSA-N 5-(aminomethyl)-n-methylfuran-3-carboxamide Chemical compound CNC(=O)C1=COC(CN)=C1 FWJJBJSRDWAPHW-UHFFFAOYSA-N 0.000 claims description 3
• FLDBJBTUVYXSJV-UHFFFAOYSA-N 5-(aminomethyl)-n-methylthiophene-3-carboxamide Chemical compound CNC(=O)C1=CSC(CN)=C1 FLDBJBTUVYXSJV-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 3
• FSKWRNINWRUSHD-UHFFFAOYSA-N methyl 2-(aminomethyl)-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(CN)=N1 FSKWRNINWRUSHD-UHFFFAOYSA-N 0.000 claims description 3
• CRMHHVVQZYELMA-UHFFFAOYSA-N methyl 2-[[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]-4-methyl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OC)SC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 CRMHHVVQZYELMA-UHFFFAOYSA-N 0.000 claims description 3
• BNCNNWWRGRSEDP-UHFFFAOYSA-N n-methyl-5-[[(2,2,2-trifluoroacetyl)amino]methyl]furan-3-carboxamide Chemical compound CNC(=O)C1=COC(CNC(=O)C(F)(F)F)=C1 BNCNNWWRGRSEDP-UHFFFAOYSA-N 0.000 claims description 3
• RSHUXWPDNREGKV-UHFFFAOYSA-N n-methyl-5-[[(2,2,2-trifluoroacetyl)amino]methyl]thiophene-3-carboxamide Chemical compound CNC(=O)C1=CSC(CNC(=O)C(F)(F)F)=C1 RSHUXWPDNREGKV-UHFFFAOYSA-N 0.000 claims description 3
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 3
• 229960003966 nicotinamide Drugs 0.000 claims description 3
• 235000005152 nicotinamide Nutrition 0.000 claims description 3
• 239000011570 nicotinamide Substances 0.000 claims description 3
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 3
• UNHWIEGKCBNIBF-UHFFFAOYSA-N tert-butyl n-[2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]carbamate Chemical compound CC1=NN=C(CCNC(=O)OC(C)(C)C)O1 UNHWIEGKCBNIBF-UHFFFAOYSA-N 0.000 claims description 3
• CUTTVDFLPQWLBT-UHFFFAOYSA-N tert-butyl n-[3-(2-acetylhydrazinyl)-3-oxopropyl]carbamate Chemical compound CC(=O)NNC(=O)CCNC(=O)OC(C)(C)C CUTTVDFLPQWLBT-UHFFFAOYSA-N 0.000 claims description 3
• XYHFNWLMOULUAT-ZDUSSCGKSA-N tert-butyl n-[[(2s)-4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methyl]carbamate Chemical compound C1CO[C@@H](CNC(=O)OC(C)(C)C)CN1CC1=CC=C(F)C(Cl)=C1 XYHFNWLMOULUAT-ZDUSSCGKSA-N 0.000 claims description 3
• HWTMFHDEXRMMSD-PYMCNQPYSA-N tert-butyl n-[[(2s)-4-[1-(3,4-difluorophenyl)ethyl]morpholin-2-yl]methyl]carbamate Chemical compound C=1C=C(F)C(F)=CC=1C(C)N1CCO[C@@H](CNC(=O)OC(C)(C)C)C1 HWTMFHDEXRMMSD-PYMCNQPYSA-N 0.000 claims description 3
• PMWQINVTMXVGNI-UHFFFAOYSA-N tert-butyl n-[[5-(methylcarbamoyl)-1,3,4-oxadiazol-2-yl]methyl]carbamate Chemical compound CNC(=O)C1=NN=C(CNC(=O)OC(C)(C)C)O1 PMWQINVTMXVGNI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 2
• KDICWNXUQADMTF-RSAXXLAASA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[4-(hydrazinecarbonyl)furan-2-yl]methyl]urea;hydrochloride Chemical compound Cl.NNC(=O)C1=COC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 KDICWNXUQADMTF-RSAXXLAASA-N 0.000 claims description 2
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical group CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-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
• 229920001367 Merrifield resin Polymers 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• 239000004793 Polystyrene Substances 0.000 claims description 2
• 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
• 229920002223 polystyrene Polymers 0.000 claims description 2
• VIYRXFZMEZXIIV-SFHVURJKSA-N tert-butyl n-[[5-[[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]furan-3-carbonyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=COC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 VIYRXFZMEZXIIV-SFHVURJKSA-N 0.000 claims description 2
• 102100024167 C-C chemokine receptor type 3 Human genes 0.000 abstract description 18
• 101710149862 C-C chemokine receptor type 3 Proteins 0.000 abstract description 18
• 239000005557 antagonist Substances 0.000 abstract description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 326
• 239000000243 solution Substances 0.000 description 115
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
• 239000000203 mixture Substances 0.000 description 91
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
• 239000002904 solvent Substances 0.000 description 80
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 54
• 238000006243 chemical reaction Methods 0.000 description 52
• 125000001424 substituent group Chemical group 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 239000007787 solid Substances 0.000 description 37
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
• 239000000725 suspension Substances 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• 235000019441 ethanol Nutrition 0.000 description 29
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 229910021529 ammonia Inorganic materials 0.000 description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• 229910052757 nitrogen Inorganic materials 0.000 description 24
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