JP2008516974A5 - - Google Patents
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- JP2008516974A5 JP2008516974A5 JP2007536972A JP2007536972A JP2008516974A5 JP 2008516974 A5 JP2008516974 A5 JP 2008516974A5 JP 2007536972 A JP2007536972 A JP 2007536972A JP 2007536972 A JP2007536972 A JP 2007536972A JP 2008516974 A5 JP2008516974 A5 JP 2008516974A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- phenyl
- pyrimidin
- ethylamino
- ethyl
- Prior art date
- 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.)
- Granted
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- -1 heterocyclenyl Chemical group 0.000 claims 218
- 150000003839 salts Chemical class 0.000 claims 48
- 239000012453 solvate Substances 0.000 claims 44
- 150000002148 esters Chemical class 0.000 claims 43
- 229940002612 prodrug Drugs 0.000 claims 42
- 239000000651 prodrug Substances 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 41
- 150000001204 N-oxides Chemical class 0.000 claims 40
- 125000001072 heteroaryl group Chemical group 0.000 claims 39
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 11
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- UVUQVKDHNYUOJX-UHFFFAOYSA-N 2h-oxadiazol-5-one;hydrochloride Chemical compound Cl.O=C1C=NNO1 UVUQVKDHNYUOJX-UHFFFAOYSA-N 0.000 claims 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 6
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- VZAYIOWOPXUAJH-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(2h-tetrazol-5-yl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C=2NN=NN=2)=NC(OC)=N1 VZAYIOWOPXUAJH-UHFFFAOYSA-N 0.000 claims 5
- BDUACRVWCKJSNP-UHFFFAOYSA-N 3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl BDUACRVWCKJSNP-UHFFFAOYSA-N 0.000 claims 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 5
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 5
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- ZZOOWTYVIVDYMY-UHFFFAOYSA-N 1-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]piperidine-3-carboxylic acid Chemical compound C=1C(N2CC(CCC2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl ZZOOWTYVIVDYMY-UHFFFAOYSA-N 0.000 claims 3
- ACMPVJVFMBJTJU-UHFFFAOYSA-N 2-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(OCC(O)=O)C=CC=2)=NC(OC)=N1 ACMPVJVFMBJTJU-UHFFFAOYSA-N 0.000 claims 3
- WLNJWBFWUGMWBZ-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]-2-methylpropanoic acid Chemical compound C=1C(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl WLNJWBFWUGMWBZ-UHFFFAOYSA-N 0.000 claims 3
- ALGPTFIVINYUHN-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methyl-1-morpholin-4-ylpropan-1-one Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)N2CCOCC2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl ALGPTFIVINYUHN-UHFFFAOYSA-N 0.000 claims 3
- FDQHHEOLVQZYFX-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methyl-n-(2h-tetrazol-5-yl)propanamide Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)NC=2NN=NN=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl FDQHHEOLVQZYFX-UHFFFAOYSA-N 0.000 claims 3
- OJJWYDBMWSIIAM-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methyl-n-(oxan-4-yl)propanamide Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)NC2CCOCC2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl OJJWYDBMWSIIAM-UHFFFAOYSA-N 0.000 claims 3
- FJKKCRCBBAXLQZ-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl FJKKCRCBBAXLQZ-UHFFFAOYSA-N 0.000 claims 3
- NMYUOSQPNAAZGM-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-n-ethylsulfonyl-2-methylpropanamide Chemical compound CCS(=O)(=O)NC(=O)C(C)(C)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 NMYUOSQPNAAZGM-UHFFFAOYSA-N 0.000 claims 3
- JRKIXXSCEPCXJI-UHFFFAOYSA-N 2-[5-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-2-oxopyridin-1-yl]acetic acid Chemical compound C=1C(C2=CN(CC(O)=O)C(=O)C=C2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl JRKIXXSCEPCXJI-UHFFFAOYSA-N 0.000 claims 3
- KCCQUXWIQVCDSB-UHFFFAOYSA-N 2-[5-[6-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]-1h-indol-3-yl]acetic acid Chemical compound C=1C(C=2C=C3C(CC(O)=O)=CNC3=CC=2)=NC(OC)=NC=1NCCC1=CC=C(C(F)(F)F)C=C1F KCCQUXWIQVCDSB-UHFFFAOYSA-N 0.000 claims 3
- ZJIWKIWBJDMSEC-UHFFFAOYSA-N 2-[[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoyl]amino]acetic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(=O)NCC(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl ZJIWKIWBJDMSEC-UHFFFAOYSA-N 0.000 claims 3
- OAXPFBVFACRFNJ-UHFFFAOYSA-N 2-[[3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]methoxy]acetic acid Chemical compound C=1C(C=2C=C(COCC(O)=O)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl OAXPFBVFACRFNJ-UHFFFAOYSA-N 0.000 claims 3
- WSWQENUVDLYIKF-UHFFFAOYSA-N 2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C(F)=CC=2)C(O)=O)=NC(OC)=N1 WSWQENUVDLYIKF-UHFFFAOYSA-N 0.000 claims 3
- ZURGISJHTAZSED-UHFFFAOYSA-N 2-methoxy-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C(OC)=CC=2)C(O)=O)=NC(OC)=N1 ZURGISJHTAZSED-UHFFFAOYSA-N 0.000 claims 3
- DUHFNHPRRSRXDQ-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(OC)C=CC=2)=NC(OC)=N1 DUHFNHPRRSRXDQ-UHFFFAOYSA-N 0.000 claims 3
- MARZXHPSGIUWTA-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[2-(4-nitrophenyl)ethyl]pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(=CC=3)[N+]([O-])=O)C=2)=C1 MARZXHPSGIUWTA-UHFFFAOYSA-N 0.000 claims 3
- XVKNAKDNRLOTHB-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[4-methoxy-3-(2h-tetrazol-5-yl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C(OC)=CC=2)C=2NN=NN=2)=NC(OC)=N1 XVKNAKDNRLOTHB-UHFFFAOYSA-N 0.000 claims 3
- CLRXANCNDUIIIT-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-quinolin-3-ylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3C=CC=CC3=NC=2)=NC(OC)=N1 CLRXANCNDUIIIT-UHFFFAOYSA-N 0.000 claims 3
- RGQYVKPVARFPAQ-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-quinolin-6-ylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3C=CC=NC3=CC=2)=NC(OC)=N1 RGQYVKPVARFPAQ-UHFFFAOYSA-N 0.000 claims 3
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims 3
- OGXUXZFREQFQOA-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]-n-methylsulfonylbenzamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C(=O)NS(C)(=O)=O)=NC(OC)=N1 OGXUXZFREQFQOA-UHFFFAOYSA-N 0.000 claims 3
- IXZMCWALJBXBNK-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzaldehyde Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=O)C=CC=2)=NC(OC)=N1 IXZMCWALJBXBNK-UHFFFAOYSA-N 0.000 claims 3
- YFMROPWTLFBMQF-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=N1 YFMROPWTLFBMQF-UHFFFAOYSA-N 0.000 claims 3
- JZMCQJRAHDQRKE-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C#N)=NC(OC)=N1 JZMCQJRAHDQRKE-UHFFFAOYSA-N 0.000 claims 3
- PBWNANNULUOGLD-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophene-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C2=C(SC=C2)C=O)=NC(OC)=N1 PBWNANNULUOGLD-UHFFFAOYSA-N 0.000 claims 3
- DYSBATRLUMHYEV-UHFFFAOYSA-N 3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenol Chemical compound C=1C(C=2C=C(O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl DYSBATRLUMHYEV-UHFFFAOYSA-N 0.000 claims 3
- ZINBWMRNPGUNCM-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(F)C=C1F ZINBWMRNPGUNCM-UHFFFAOYSA-N 0.000 claims 3
- SLAZZBLUJYRPBZ-UHFFFAOYSA-N 3-[6-[2-(2,6-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=C(Cl)C=CC=C1Cl SLAZZBLUJYRPBZ-UHFFFAOYSA-N 0.000 claims 3
- HIOIGVQTLIDZOZ-UHFFFAOYSA-N 3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl HIOIGVQTLIDZOZ-UHFFFAOYSA-N 0.000 claims 3
- HUJFQFSPBCWPSS-UHFFFAOYSA-N 4-[3-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]phenyl]-n-methylsulfonyloxane-4-carboxamide Chemical compound C=1C(C=2C=C(C=CC=2)C2(CCOCC2)C(=O)NS(C)(=O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 HUJFQFSPBCWPSS-UHFFFAOYSA-N 0.000 claims 3
- SEIWEJOFJBQCEQ-UHFFFAOYSA-N 4-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-n-methylsulfonyloxane-4-carboxamide Chemical compound C=1C(C=2C=C(C=CC=2)C2(CCOCC2)C(=O)NS(C)(=O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl SEIWEJOFJBQCEQ-UHFFFAOYSA-N 0.000 claims 3
- QBDCAGNZOIEWRB-UHFFFAOYSA-N 4-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]oxane-4-carboxylic acid Chemical compound C=1C(C=2C=C(C=CC=2)C2(CCOCC2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl QBDCAGNZOIEWRB-UHFFFAOYSA-N 0.000 claims 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 3
- CJNDNNNIPYNXEG-UHFFFAOYSA-N 5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophene-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(C=O)=CC=2)=NC(OC)=N1 CJNDNNNIPYNXEG-UHFFFAOYSA-N 0.000 claims 3
- WXNPFPVBMGITTR-UHFFFAOYSA-N 5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(=CC=2)C(O)=O)=NC(OC)=N1 WXNPFPVBMGITTR-UHFFFAOYSA-N 0.000 claims 3
- DTHZQOUUABRDHW-UHFFFAOYSA-N 6-(1h-indazol-6-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3NN=CC3=CC=2)=NC(OC)=N1 DTHZQOUUABRDHW-UHFFFAOYSA-N 0.000 claims 3
- YRFMYYYNKZMPKB-UHFFFAOYSA-N 6-(1h-indol-5-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3C=CNC3=CC=2)=NC(OC)=N1 YRFMYYYNKZMPKB-UHFFFAOYSA-N 0.000 claims 3
- KRTKZRNRTAYUEY-UHFFFAOYSA-N N-[1-[5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]ethylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(=CC=2)C(C)=NO)=NC(OC)=N1 KRTKZRNRTAYUEY-UHFFFAOYSA-N 0.000 claims 3
- NFWQTSFQMUZWGI-UHFFFAOYSA-N N-[[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]methylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C2=C(SC=C2)C=NO)=NC(OC)=N1 NFWQTSFQMUZWGI-UHFFFAOYSA-N 0.000 claims 3
- HAUGUPYUNVUQCZ-UHFFFAOYSA-N N-[[5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]methylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(C=NO)=CC=2)=NC(OC)=N1 HAUGUPYUNVUQCZ-UHFFFAOYSA-N 0.000 claims 3
- LJRUUYYUQSPNJI-UHFFFAOYSA-N [3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methanol Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CO)C=CC=2)=NC(OC)=N1 LJRUUYYUQSPNJI-UHFFFAOYSA-N 0.000 claims 3
- RVKDICMOKSXTNL-UHFFFAOYSA-N [3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl] n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 RVKDICMOKSXTNL-UHFFFAOYSA-N 0.000 claims 3
- BZLVZAWKTIULOB-UHFFFAOYSA-N [5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(CO)=CC=2)=NC(OC)=N1 BZLVZAWKTIULOB-UHFFFAOYSA-N 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- AAYUCSUEYKDIEG-UHFFFAOYSA-N chembl1644237 Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C(=CC=CC=2)O)=NC(OC)=N1 AAYUCSUEYKDIEG-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 3
- IPFRJRQDYKFUPG-UHFFFAOYSA-N methyl 2-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 IPFRJRQDYKFUPG-UHFFFAOYSA-N 0.000 claims 3
- LIIFDNXCGKXBGG-UHFFFAOYSA-N methyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 LIIFDNXCGKXBGG-UHFFFAOYSA-N 0.000 claims 3
- RDRBMBPTINTCSN-UHFFFAOYSA-N methyl n-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 RDRBMBPTINTCSN-UHFFFAOYSA-N 0.000 claims 3
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- RTLZXVVAKGXFSB-UHFFFAOYSA-N n-benzylsulfonyl-2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanamide Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl RTLZXVVAKGXFSB-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- JIPFGDSGYZHZQZ-IBGZPJMESA-N (2s)-2-[[2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-yl]amino]-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(O)=O)NC1=CC(C=2C=C(OC)C=CC=2)=NC(OC)=N1 JIPFGDSGYZHZQZ-IBGZPJMESA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- MIDXFMMNLJOEGD-UHFFFAOYSA-N 1-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C(C)=O)=NC(OC)=N1 MIDXFMMNLJOEGD-UHFFFAOYSA-N 0.000 claims 2
- KVUBQMZZSUGHGH-UHFFFAOYSA-N 1-[4-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=CC(=CC=2)C(C)=O)=NC(OC)=N1 KVUBQMZZSUGHGH-UHFFFAOYSA-N 0.000 claims 2
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- VKXVHIWOFDKOPX-UHFFFAOYSA-N 1-ethyl-3-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]urea Chemical compound CCNC(=O)NC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 VKXVHIWOFDKOPX-UHFFFAOYSA-N 0.000 claims 2
- 125000004564 2,3-dihydrobenzofuran-2-yl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 2
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- IPPGLWFBERIWET-UHFFFAOYSA-N 2-[3-[6-(3,4-dihydro-1h-isochromen-1-ylmethylamino)-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NCC2C3=CC=CC=C3CCO2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 IPPGLWFBERIWET-UHFFFAOYSA-N 0.000 claims 2
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- KPAHENOYQQCZCR-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]acetonitrile Chemical compound C=1C(C=2C=C(CC#N)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl KPAHENOYQQCZCR-UHFFFAOYSA-N 0.000 claims 2
- ZCDCFCQGWRMVMJ-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(C)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl ZCDCFCQGWRMVMJ-UHFFFAOYSA-N 0.000 claims 2
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- VDWQTKKALSMAKV-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 VDWQTKKALSMAKV-UHFFFAOYSA-N 0.000 claims 2
- BIASCFWSJVVCQP-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C(N)=O)=NC(OC)=N1 BIASCFWSJVVCQP-UHFFFAOYSA-N 0.000 claims 2
- SNQFYTGSLPIDJG-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)S(N)(=O)=O)=NC(OC)=N1 SNQFYTGSLPIDJG-UHFFFAOYSA-N 0.000 claims 2
- HJBWADJKSXOZJT-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(O)C=CC=2)=NC(OC)=N1 HJBWADJKSXOZJT-UHFFFAOYSA-N 0.000 claims 2
- ZGYVACPEJAGXPM-UHFFFAOYSA-N 3-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 ZGYVACPEJAGXPM-UHFFFAOYSA-N 0.000 claims 2
- IMXIOVJMDHVPPK-UHFFFAOYSA-N 3-[6-[2-(2,2-difluoro-1,3-benzodioxol-5-yl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound N=1C(OC)=NC(NCCC=2C=C3OC(F)(F)OC3=CC=2)=CC=1C1=CC=CC(C(O)=O)=C1 IMXIOVJMDHVPPK-UHFFFAOYSA-N 0.000 claims 2
- RADNMCGCMBSLHM-UHFFFAOYSA-N 3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzaldehyde Chemical compound C=1C(C=2C=C(C=O)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl RADNMCGCMBSLHM-UHFFFAOYSA-N 0.000 claims 2
- VUYUOIVSOGLPDO-UHFFFAOYSA-N 3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl VUYUOIVSOGLPDO-UHFFFAOYSA-N 0.000 claims 2
- RIPBUXHGBDABRR-UHFFFAOYSA-N 3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenol Chemical compound C=1C(C=2C=C(O)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl RIPBUXHGBDABRR-UHFFFAOYSA-N 0.000 claims 2
- FBMJKHRWSZLGBX-UHFFFAOYSA-N 3-[6-[2-(3,4-dimethoxyphenyl)ethylamino]-2-methoxypyrimidin-4-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C=1C(C=2C=C(C=CC=2)C(=O)NCCN2CCCC2)=NC(OC)=NC=1NCCC1=CC=C(OC)C(OC)=C1 FBMJKHRWSZLGBX-UHFFFAOYSA-N 0.000 claims 2
- SBZWOUPXZCKUFD-UHFFFAOYSA-N 3-[6-[2-(3,4-dimethoxyphenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC)C(OC)=C1 SBZWOUPXZCKUFD-UHFFFAOYSA-N 0.000 claims 2
- QMFYZORHTUFQLM-UHFFFAOYSA-N 3-[6-[2-(3,4-dimethoxyphenyl)ethylamino]-2-methylsulfanylpyrimidin-4-yl]benzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C(O)=O)=NC(SC)=N1 QMFYZORHTUFQLM-UHFFFAOYSA-N 0.000 claims 2
- LDKQGCBQVPIRIJ-UHFFFAOYSA-N 3-[6-[2-(3-fluoro-4-methoxyphenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzonitrile Chemical compound C=1C(C=2C=C(C=CC=2)C#N)=NC(OC)=NC=1NCCC1=CC=C(OC)C(F)=C1 LDKQGCBQVPIRIJ-UHFFFAOYSA-N 0.000 claims 2
- UIKAQUIGLUITSY-UHFFFAOYSA-N 3-[6-[2-(4-chlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1 UIKAQUIGLUITSY-UHFFFAOYSA-N 0.000 claims 2
- WXLKZEROFYSHPU-UHFFFAOYSA-N 3-[6-[2-(4-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(F)C=C1 WXLKZEROFYSHPU-UHFFFAOYSA-N 0.000 claims 2
- WJPJBNRAIKENGV-UHFFFAOYSA-N 4-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=CC(=CC=2)C(N)=O)=NC(OC)=N1 WJPJBNRAIKENGV-UHFFFAOYSA-N 0.000 claims 2
- JIBMNNUBTNVLBG-UHFFFAOYSA-N 4-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophene-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=O)SC=2)=NC(OC)=N1 JIBMNNUBTNVLBG-UHFFFAOYSA-N 0.000 claims 2
- ANZXVFDVMDGOGU-UHFFFAOYSA-N 5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]-n-methylthiophene-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(=O)NC)=CC=C1C1=CC(NCCC=2C=CC(OC)=CC=2)=NC(OC)=N1 ANZXVFDVMDGOGU-UHFFFAOYSA-N 0.000 claims 2
- VXJQOIHGRGLPPT-UHFFFAOYSA-N 5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(=CC=2)C(O)=O)=NC(OC)=N1 VXJQOIHGRGLPPT-UHFFFAOYSA-N 0.000 claims 2
- KWQLREQKWFHGMW-UHFFFAOYSA-N 5-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C=1C(C=2SC(=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl KWQLREQKWFHGMW-UHFFFAOYSA-N 0.000 claims 2
- JXTPMOZXNLPMTP-UHFFFAOYSA-N 5-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-1h-pyridin-2-one Chemical compound C=1C(C2=CNC(=O)C=C2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl JXTPMOZXNLPMTP-UHFFFAOYSA-N 0.000 claims 2
- HHJYNTGIGSDIHZ-UHFFFAOYSA-N 5-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methylsulfanylpyrimidin-4-yl]-1h-pyridin-2-one Chemical compound C=1C(C2=CNC(=O)C=C2)=NC(SC)=NC=1NCCC1=C(F)C=CC=C1Cl HHJYNTGIGSDIHZ-UHFFFAOYSA-N 0.000 claims 2
- HFSLQDCXJLAUQF-UHFFFAOYSA-N 5-[[3-[6-[2-(3,4-difluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]methyl]-1-ethyl-1,2,4-triazolidin-3-one Chemical compound CCN1NC(=O)NC1COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=C(F)C(F)=CC=3)C=2)=C1 HFSLQDCXJLAUQF-UHFFFAOYSA-N 0.000 claims 2
- GYWQFXDSZVIMIP-UHFFFAOYSA-N 6-(1-benzothiophen-2-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC3=CC=CC=C3C=2)=NC(OC)=N1 GYWQFXDSZVIMIP-UHFFFAOYSA-N 0.000 claims 2
- VSYGQPAEKKQRMF-UHFFFAOYSA-N 6-(2,3-dihydro-1-benzofuran-5-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3CCOC3=CC=2)=NC(OC)=N1 VSYGQPAEKKQRMF-UHFFFAOYSA-N 0.000 claims 2
- FNRAUILVXITILG-UHFFFAOYSA-N 6-(2h-benzotriazol-5-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3N=NNC3=CC=2)=NC(OC)=N1 FNRAUILVXITILG-UHFFFAOYSA-N 0.000 claims 2
- BBOUWWHFYOBFNA-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]-2-ethoxypyrimidin-4-amine Chemical compound C=1C(C=2C=C(OC)C(OC)=CC=2)=NC(OCC)=NC=1NCCC1=CC=C(OC)C(OC)=C1 BBOUWWHFYOBFNA-UHFFFAOYSA-N 0.000 claims 2
- HBUNUWKPQZOIPB-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]-2-methylsulfanylpyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C=2C=C(OC)C(OC)=CC=2)=NC(SC)=N1 HBUNUWKPQZOIPB-UHFFFAOYSA-N 0.000 claims 2
- BMEBULCQADRRIG-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]-2-propan-2-yloxypyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=CC(C=2C=C(OC)C(OC)=CC=2)=NC(OC(C)C)=N1 BMEBULCQADRRIG-UHFFFAOYSA-N 0.000 claims 2
- HWEJZIJOSYUCKX-UHFFFAOYSA-N 6-(3,5-dimethyl-1,2-oxazol-4-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C2=C(ON=C2C)C)=NC(OC)=N1 HWEJZIJOSYUCKX-UHFFFAOYSA-N 0.000 claims 2
- CYTVDSJKELGJQV-UHFFFAOYSA-N 6-(3-aminophenyl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(N)C=CC=2)=NC(OC)=N1 CYTVDSJKELGJQV-UHFFFAOYSA-N 0.000 claims 2
- BWFPUWQZRPOASM-UHFFFAOYSA-N 6-(3-methoxyphenyl)-n-[2-(4-methoxyphenyl)ethyl]-2-methylsulfanylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(OC)C=CC=2)=NC(SC)=N1 BWFPUWQZRPOASM-UHFFFAOYSA-N 0.000 claims 2
- MBLQOQCEPSWDGX-UHFFFAOYSA-N 6-(3h-benzimidazol-5-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3N=CNC3=CC=2)=NC(OC)=N1 MBLQOQCEPSWDGX-UHFFFAOYSA-N 0.000 claims 2
- HCGPNAZEXVWUKL-UHFFFAOYSA-N 6-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3OC(=O)NC3=CC=2)=NC(OC)=N1 HCGPNAZEXVWUKL-UHFFFAOYSA-N 0.000 claims 2
- ICYPTMNUYMAVJH-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=CC(=CC=2)N(C)C)=NC(OC)=N1 ICYPTMNUYMAVJH-UHFFFAOYSA-N 0.000 claims 2
- VTAGZIVXIZBHDV-UHFFFAOYSA-N 6-[5-(difluoromethyl)thiophen-2-yl]-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(=CC=2)C(F)F)=NC(OC)=N1 VTAGZIVXIZBHDV-UHFFFAOYSA-N 0.000 claims 2
- XPYMCUZYEYRYHF-UHFFFAOYSA-N 6-isoquinolin-5-yl-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C3=CC=NC=C3C=CC=2)=NC(OC)=N1 XPYMCUZYEYRYHF-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229940124003 CRTH2 antagonist Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 2
- AYOGOCPFJWNTPT-UHFFFAOYSA-N [3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C2=C(SC=C2)CO)=NC(OC)=N1 AYOGOCPFJWNTPT-UHFFFAOYSA-N 0.000 claims 2
- GROKCWWQXCVBOT-UHFFFAOYSA-N [3-[3-chloro-4-[2-[[6-[3-(hydroxymethyl)phenyl]-2-methoxypyrimidin-4-yl]amino]ethyl]phenyl]phenyl]methanol Chemical compound C=1C(C=2C=C(CO)C=CC=2)=NC(OC)=NC=1NCCC(C(=C1)Cl)=CC=C1C1=CC=CC(CO)=C1 GROKCWWQXCVBOT-UHFFFAOYSA-N 0.000 claims 2
- DZSCWOZAGMMWKI-UHFFFAOYSA-N [3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]methanol Chemical compound C=1C(C=2C=C(CO)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl DZSCWOZAGMMWKI-UHFFFAOYSA-N 0.000 claims 2
- JWQXUEILRDTIOW-UHFFFAOYSA-N [3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]methanol Chemical compound C=1C(C=2C=C(CO)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl JWQXUEILRDTIOW-UHFFFAOYSA-N 0.000 claims 2
- DNQCCEJPZARAQO-UHFFFAOYSA-N [6-(1h-indol-6-yl)-2-methoxypyrimidin-4-yl]-[2-(4-methoxyphenyl)ethyl]azanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1CC[NH2+]C1=CC(C=2C=C3NC=CC3=CC=2)=NC(OC)=N1 DNQCCEJPZARAQO-UHFFFAOYSA-N 0.000 claims 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical group CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000001387 anti-histamine Effects 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 229940125388 beta agonist Drugs 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- NUMWMQMSYPKIMB-UHFFFAOYSA-N ethyl 2-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 NUMWMQMSYPKIMB-UHFFFAOYSA-N 0.000 claims 2
- GJWSJYCDOPWSND-UHFFFAOYSA-N ethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)OC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 GJWSJYCDOPWSND-UHFFFAOYSA-N 0.000 claims 2
- CZFXBKRFSUATDD-UHFFFAOYSA-N ethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 CZFXBKRFSUATDD-UHFFFAOYSA-N 0.000 claims 2
- AZJSWALBALDYFL-UHFFFAOYSA-N ethyl 2-[[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 AZJSWALBALDYFL-UHFFFAOYSA-N 0.000 claims 2
- ZVPOVBZPJYEEGF-UHFFFAOYSA-N ethyl 2-chloro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 ZVPOVBZPJYEEGF-UHFFFAOYSA-N 0.000 claims 2
- RKYMFZYNRQRJOY-UHFFFAOYSA-N ethyl 3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 RKYMFZYNRQRJOY-UHFFFAOYSA-N 0.000 claims 2
- POMKEIIJSDSFDA-UHFFFAOYSA-N ethyl 4-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]oxane-4-carboxylate Chemical compound C=1C=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=CC=1C1(C(=O)OCC)CCOCC1 POMKEIIJSDSFDA-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- JZIUIBASGRASSA-UHFFFAOYSA-N ethyl n-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 JZIUIBASGRASSA-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- QQEXQQJBCNDEKG-UHFFFAOYSA-N methyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 QQEXQQJBCNDEKG-UHFFFAOYSA-N 0.000 claims 2
- KHARTMVADHNSCA-UHFFFAOYSA-N methyl 2-[5-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-2-oxopyridin-1-yl]acetate Chemical compound C1=CC(=O)N(CC(=O)OC)C=C1C1=CC(NCCC=2C(=CC=CC=2F)Cl)=NC(OC)=N1 KHARTMVADHNSCA-UHFFFAOYSA-N 0.000 claims 2
- RBONOMPESPZWNN-UHFFFAOYSA-N methyl 3-[6-[2-(3,4-dimethoxyphenyl)ethylamino]-2-methoxypyrimidin-4-yl]oxybenzoate Chemical compound COC(=O)C1=CC=CC(OC=2N=C(OC)N=C(NCCC=3C=C(OC)C(OC)=CC=3)C=2)=C1 RBONOMPESPZWNN-UHFFFAOYSA-N 0.000 claims 2
- YGXRYJBXZWZHPU-UHFFFAOYSA-N methyl 4-[3-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]phenyl]oxane-4-carboxylate Chemical compound C=1C=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC(F)(F)F)=CC=3)C=2)=CC=1C1(C(=O)OC)CCOCC1 YGXRYJBXZWZHPU-UHFFFAOYSA-N 0.000 claims 2
- DNVQIKOMPOMUHD-UHFFFAOYSA-N n-[1-(4-chlorophenyl)propan-2-yl]-6-(3,4-dimethoxyphenyl)-2-methoxypyrimidin-4-amine Chemical compound C=1C(C=2C=C(OC)C(OC)=CC=2)=NC(OC)=NC=1NC(C)CC1=CC=C(Cl)C=C1 DNVQIKOMPOMUHD-UHFFFAOYSA-N 0.000 claims 2
- HDOVMCHUSVBDBO-UHFFFAOYSA-N n-[2-(1h-imidazol-5-yl)ethyl]-2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3N=CNC=3)C=2)=C1 HDOVMCHUSVBDBO-UHFFFAOYSA-N 0.000 claims 2
- QJLYXAZELRWYMO-UHFFFAOYSA-N n-[2-(2-chloro-6-fluorophenyl)ethyl]-6-(6-methoxypyridin-3-yl)-2-methylsulfanylpyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(NCCC=2C(=CC=CC=2F)Cl)=NC(SC)=N1 QJLYXAZELRWYMO-UHFFFAOYSA-N 0.000 claims 2
- CYRRQVBZVSRFRH-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-methoxy-6-(4-phenylphenyl)pyrimidin-4-amine Chemical compound C=1C(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC(OC)=NC=1NCCC1=CC=C(OC)C(OC)=C1 CYRRQVBZVSRFRH-UHFFFAOYSA-N 0.000 claims 2
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| GB1143167A (en) * | 1967-01-25 | 1969-02-19 | Ucb Sa | Derivatives of pyrimidine |
| DE4031792A1 (de) * | 1990-10-08 | 1991-04-25 | Franz Reiner Dipl Phy Thedieck | Indikator-element aus festen bestandteilen |
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| GB9806739D0 (en) * | 1998-03-28 | 1998-05-27 | Univ Newcastle Ventures Ltd | Cyclin dependent kinase inhibitors |
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| DE10006453A1 (de) | 2000-02-14 | 2001-08-16 | Bayer Ag | Piperidylcarbonsäuren als Integrinantagonisten |
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| US20040087590A1 (en) * | 2002-08-23 | 2004-05-06 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
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| WO2004017922A2 (en) * | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
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| MXPA06000771A (es) * | 2003-07-25 | 2006-04-18 | Ciba Sc Holding Ag | Uso de 2,4-bis(alquilamino)-pirimidinas o -quinazolinas substituidas como antimicrobianos. |
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| US7507826B2 (en) * | 2004-03-30 | 2009-03-24 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of JAK and other protein kinases |
| CA2581623A1 (en) * | 2004-09-23 | 2006-03-30 | Reddy Us Therapeutics, Inc. | Novel pyridine compounds, process for their preparation and compositions containing them |
| ZA200704888B (en) * | 2004-11-22 | 2009-02-25 | Vertex Pharma | Pyrrolopyrazines and pyrazolopyrazines useful as inhibitors of protein kinases |
| JP2008534472A (ja) * | 2005-03-22 | 2008-08-28 | ノイロサーチ アクティーゼルスカブ | カリウムチャンネル調節剤としてのピラゾリル−ピリミジン及びその医学的使用 |
| GT200600457A (es) * | 2005-10-13 | 2007-04-27 | Aventis Pharma Inc | Sal de fosfato dihidrogeno como antagonistas del receptor de prostaglandina d2 |
-
2005
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- 2005-10-14 AU AU2005295502A patent/AU2005295502B2/en not_active Ceased
- 2005-10-14 MX MX2007003155A patent/MX2007003155A/es active IP Right Grant
- 2005-10-14 DK DK05812481.9T patent/DK1891019T3/da active
- 2005-10-14 UA UAA200705281A patent/UA88485C2/ru unknown
- 2005-10-14 BR BRPI0516482-6A patent/BRPI0516482A/pt not_active Application Discontinuation
- 2005-10-14 PT PT05812481T patent/PT1891019E/pt unknown
- 2005-10-14 SI SI200531599T patent/SI1891019T1/sl unknown
- 2005-10-14 KR KR1020077011039A patent/KR101280268B1/ko not_active Expired - Fee Related
- 2005-10-14 TW TW094135790A patent/TWI372751B/zh not_active IP Right Cessation
- 2005-10-14 CN CN2005800353962A patent/CN101039920B/zh not_active Expired - Fee Related
- 2005-10-14 WO PCT/US2005/037148 patent/WO2006044732A2/en not_active Ceased
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2007
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