JP2008516974A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
- WJXFPYRZBRXTOU-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-6-[3-[difluoro(2h-tetrazol-5-yl)methyl]phenyl]-2-methoxypyrimidin-4-amine Chemical compound C=1C(C=2C=C(C=CC=2)C(F)(F)C=2NN=NN=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl WJXFPYRZBRXTOU-UHFFFAOYSA-N 0.000 claims 3
- KHYILGODOLKZDQ-UHFFFAOYSA-N n-[[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=NO)C=CC=2)=NC(OC)=N1 KHYILGODOLKZDQ-UHFFFAOYSA-N 0.000 claims 3
- 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
- LRLGNTCDJDTTQE-UHFFFAOYSA-N 1-[5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(=CC=2)C(C)=O)=NC(OC)=N1 LRLGNTCDJDTTQE-UHFFFAOYSA-N 0.000 claims 2
- BYAWAXOLOBCSIC-UHFFFAOYSA-N 1-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]piperidine-4-carboxylic acid Chemical compound C=1C(N2CCC(CC2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl BYAWAXOLOBCSIC-UHFFFAOYSA-N 0.000 claims 2
- 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
- MKNYIFUKTYKRDM-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)OCC(O)CO)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl MKNYIFUKTYKRDM-UHFFFAOYSA-N 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- GMGBZDNIBPOYDF-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethyl 3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoate Chemical compound C=1C(C=2C=C(C=CC=2)C(=O)OCCN2CCN(C)CC2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl GMGBZDNIBPOYDF-UHFFFAOYSA-N 0.000 claims 2
- RCGHCTYUKHOASN-UHFFFAOYSA-N 2-[2-chloro-5-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]propan-2-ol Chemical compound C=1C(C=2C=C(C(Cl)=CC=2)C(C)(C)O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl RCGHCTYUKHOASN-UHFFFAOYSA-N 0.000 claims 2
- RKEVYFRTIOZLFU-UHFFFAOYSA-N 2-[2-fluoro-5-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound C=1C(C=2C=C(C(F)=CC=2)C(C)(C)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 RKEVYFRTIOZLFU-UHFFFAOYSA-N 0.000 claims 2
- MYEPQPUVVMYDLR-UHFFFAOYSA-N 2-[3-[2-methoxy-6-(thiophen-3-ylmethylamino)pyrimidin-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=1NCC=1C=CSC=1 MYEPQPUVVMYDLR-UHFFFAOYSA-N 0.000 claims 2
- RPEQGHCMCBLHDW-UHFFFAOYSA-N 2-[3-[2-methoxy-6-[(4-methyl-2,3-dihydro-1,4-benzoxazin-2-yl)methylamino]pyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NCC2OC3=CC=CC=C3N(C)C2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 RPEQGHCMCBLHDW-UHFFFAOYSA-N 0.000 claims 2
- XDSZVOXSKTXXHF-UHFFFAOYSA-N 2-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)=NC(OC)=N1 XDSZVOXSKTXXHF-UHFFFAOYSA-N 0.000 claims 2
- MNFHQAYZTGXMDS-UHFFFAOYSA-N 2-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]acetonitrile Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CC#N)C=CC=2)=NC(OC)=N1 MNFHQAYZTGXMDS-UHFFFAOYSA-N 0.000 claims 2
- LMBKKFWBOACGPS-UHFFFAOYSA-N 2-[3-[6-(1-benzofuran-5-ylmethylamino)-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NCC=2C=C3C=COC3=CC=2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 LMBKKFWBOACGPS-UHFFFAOYSA-N 0.000 claims 2
- BQZOACSDDWVPIG-UHFFFAOYSA-N 2-[3-[6-(2,3-dihydro-1-benzofuran-2-ylmethylamino)-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NCC2OC3=CC=CC=C3C2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 BQZOACSDDWVPIG-UHFFFAOYSA-N 0.000 claims 2
- QMZWWHUFQRZCDD-UHFFFAOYSA-N 2-[3-[6-(2,3-dihydro-1h-inden-1-ylamino)-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NC2C3=CC=CC=C3CC2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 QMZWWHUFQRZCDD-UHFFFAOYSA-N 0.000 claims 2
- FSYHKILGBNONNL-UHFFFAOYSA-N 2-[3-[6-(2,3-dihydro-1h-inden-2-ylamino)-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(OC)=NC(NC2CC3=CC=CC=C3C2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 FSYHKILGBNONNL-UHFFFAOYSA-N 0.000 claims 2
- 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
- MUJSAJMEUKIZNS-UHFFFAOYSA-N 2-[3-[6-[(2,2-difluoro-2-phenylethyl)amino]-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=1NCC(F)(F)C1=CC=CC=C1 MUJSAJMEUKIZNS-UHFFFAOYSA-N 0.000 claims 2
- QELFOVKXCXHGPL-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-(hydroxymethyl)pyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC(C=2N=C(CO)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 QELFOVKXCXHGPL-UHFFFAOYSA-N 0.000 claims 2
- SBPWDGHALBJDEV-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-(methoxymethyl)pyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(O)=O)=NC(COC)=NC=1NCCC1=CC=C(Cl)C=C1Cl SBPWDGHALBJDEV-UHFFFAOYSA-N 0.000 claims 2
- IGDFJTDYWIFESA-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]acetonitrile Chemical compound C=1C(C=2C=C(OCC#N)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl IGDFJTDYWIFESA-UHFFFAOYSA-N 0.000 claims 2
- VKRKYQYUIYHBOO-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2,2-difluoroacetic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(F)(F)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl VKRKYQYUIYHBOO-UHFFFAOYSA-N 0.000 claims 2
- JFAROGNTZJARCZ-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2,2-difluoroacetonitrile Chemical compound C=1C(C=2C=C(C=CC=2)C(F)(F)C#N)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl JFAROGNTZJARCZ-UHFFFAOYSA-N 0.000 claims 2
- XIFPOWZZZAKHFE-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(C)(C)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl XIFPOWZZZAKHFE-UHFFFAOYSA-N 0.000 claims 2
- 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
- BWZOSWSEPRAAST-UHFFFAOYSA-N 2-[3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]acetonitrile Chemical compound C=1C(C=2C=C(OCC#N)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl BWZOSWSEPRAAST-UHFFFAOYSA-N 0.000 claims 2
- AXQLHCOQVJHFRJ-UHFFFAOYSA-N 2-chloro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C(Cl)=CC=2)C(O)=O)=NC(OC)=N1 AXQLHCOQVJHFRJ-UHFFFAOYSA-N 0.000 claims 2
- UHCMTJMNYLBSAI-UHFFFAOYSA-N 2-ethyl-6-(3-methoxyphenyl)-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C=1C(C=2C=C(OC)C=CC=2)=NC(CC)=NC=1NCCC1=CC=C(OC)C=C1 UHCMTJMNYLBSAI-UHFFFAOYSA-N 0.000 claims 2
- RCQXNMOTBJJJSR-UHFFFAOYSA-N 2-fluoro-5-[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(F)=CC=2)=NC(OC)=N1 RCQXNMOTBJJJSR-UHFFFAOYSA-N 0.000 claims 2
- LSTZTTLARHOHGY-UHFFFAOYSA-N 2-methoxy-5-[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(OC)=CC=2)=NC(OC)=N1 LSTZTTLARHOHGY-UHFFFAOYSA-N 0.000 claims 2
- AIMFCSQKZKOPNS-UHFFFAOYSA-N 2-methoxy-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzonitrile Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C(OC)=CC=2)C#N)=NC(OC)=N1 AIMFCSQKZKOPNS-UHFFFAOYSA-N 0.000 claims 2
- DGHCNCMLFFBEEI-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[2-(4-methoxyphenyl)-2-methylpropyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(C)(C)CNC1=CC(C=2C=C(OC)C=CC=2)=NC(OC)=N1 DGHCNCMLFFBEEI-UHFFFAOYSA-N 0.000 claims 2
- LXMJQLAWLGEVMM-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 LXMJQLAWLGEVMM-UHFFFAOYSA-N 0.000 claims 2
- DIICPOQPLGGFEO-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(1,3-oxazol-5-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2OC=NC=2)=NC(OC)=N1 DIICPOQPLGGFEO-UHFFFAOYSA-N 0.000 claims 2
- OAKHNVOGNFAMBA-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(1-methylindol-5-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3C=CN(C)C3=CC=2)=NC(OC)=N1 OAKHNVOGNFAMBA-UHFFFAOYSA-N 0.000 claims 2
- NFKWKXJENHRVPZ-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(1h-pyrazol-4-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C2=CNN=C2)=NC(OC)=N1 NFKWKXJENHRVPZ-UHFFFAOYSA-N 0.000 claims 2
- IGZMGPZHXBYBIX-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(3-methylsulfonylphenyl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=NC(OC)=N1 IGZMGPZHXBYBIX-UHFFFAOYSA-N 0.000 claims 2
- BZXYLLKICRAQTA-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(4-morpholin-4-ylphenyl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=CC(=CC=2)N2CCOCC2)=NC(OC)=N1 BZXYLLKICRAQTA-UHFFFAOYSA-N 0.000 claims 2
- ZCEDHPVVZXRWOW-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2OC(C)=NN=2)=NC(OC)=N1 ZCEDHPVVZXRWOW-UHFFFAOYSA-N 0.000 claims 2
- HAWMPRDKLCDHIP-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(5-methylthiophen-2-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(C)=CC=2)=NC(OC)=N1 HAWMPRDKLCDHIP-UHFFFAOYSA-N 0.000 claims 2
- IYUGNIIQZKEROI-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-(6-methoxypyridin-3-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=NC(OC)=CC=2)=NC(OC)=N1 IYUGNIIQZKEROI-UHFFFAOYSA-N 0.000 claims 2
- HOMZAIMLKOFHHM-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(2h-tetrazol-5-ylmethyl)phenyl]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CC=3NN=NN=3)C=CC=2)=NC(OC)=N1 HOMZAIMLKOFHHM-UHFFFAOYSA-N 0.000 claims 2
- GKSSZYQAUXFHQH-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C=2ON=C(C)C=2)=NC(OC)=N1 GKSSZYQAUXFHQH-UHFFFAOYSA-N 0.000 claims 2
- RAIGYPOOQXEBSX-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(5-methyl-1h-pyrazol-3-yl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C=2NN=C(C)C=2)=NC(OC)=N1 RAIGYPOOQXEBSX-UHFFFAOYSA-N 0.000 claims 2
- HOOOPNKRMSQQGO-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[5-(pyrrolidin-1-ylmethyl)thiophen-2-yl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2SC(CN3CCCC3)=CC=2)=NC(OC)=N1 HOOOPNKRMSQQGO-UHFFFAOYSA-N 0.000 claims 2
- OUQPGYJVBNXCGA-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-pyridin-3-ylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=NC=CC=2)=NC(OC)=N1 OUQPGYJVBNXCGA-UHFFFAOYSA-N 0.000 claims 2
- YAERPSMUSSCSDX-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-pyridin-4-ylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=CN=CC=2)=NC(OC)=N1 YAERPSMUSSCSDX-UHFFFAOYSA-N 0.000 claims 2
- HJFDCMKUYBPOJP-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]benzoate Chemical compound C=1C(C=2C=C(C=CC=2)C(=O)OCCN2CCOCC2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl HJFDCMKUYBPOJP-UHFFFAOYSA-N 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 2
- OXTWAHXILRDBGE-UHFFFAOYSA-N 3-[2-[[2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-yl]amino]ethyl]-1h-indol-5-ol Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C4=CC(O)=CC=C4NC=3)C=2)=C1 OXTWAHXILRDBGE-UHFFFAOYSA-N 0.000 claims 2
- 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
- MDALPOMPPTUTQS-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-6-(furan-2-yl)-2-methoxypyrimidin-4-amine Chemical compound C=1C(C=2OC=CC=2)=NC(OC)=NC=1NCCC1=CC=C(OC)C(OC)=C1 MDALPOMPPTUTQS-UHFFFAOYSA-N 0.000 claims 2
- ZMCWEAOEFZIGCP-UHFFFAOYSA-N n-[2-(3-fluoro-4-methoxyphenyl)ethyl]-2-methoxy-6-[3-(2h-tetrazol-5-yl)phenyl]pyrimidin-4-amine Chemical compound C=1C(C=2C=C(C=CC=2)C2=NNN=N2)=NC(OC)=NC=1NCCC1=CC=C(OC)C(F)=C1 ZMCWEAOEFZIGCP-UHFFFAOYSA-N 0.000 claims 2
- HESJKZGPFSQMJL-UHFFFAOYSA-N n-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2-methoxy-6-[3-(oxiran-2-ylmethoxy)phenyl]pyrimidin-4-amine Chemical compound C=1C(C=2C=C(OCC3OC3)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(C(F)(F)F)C=C1F HESJKZGPFSQMJL-UHFFFAOYSA-N 0.000 claims 2
- RCLVWVYAVJKICJ-UHFFFAOYSA-N n-[2-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C(=CC=CC=2)NS(C)(=O)=O)=NC(OC)=N1 RCLVWVYAVJKICJ-UHFFFAOYSA-N 0.000 claims 2
- IVQMZCJXCYTPQQ-UHFFFAOYSA-N n-[2-[3-[6-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]phenyl]ethyl]-2-methoxyacetamide Chemical compound COCC(=O)NCCC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(=CC=3)C(F)(F)F)F)C=2)=C1 IVQMZCJXCYTPQQ-UHFFFAOYSA-N 0.000 claims 2
- LTBGKOAIOJDRJO-UHFFFAOYSA-N n-[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(NC(C)=O)C=CC=2)=NC(OC)=N1 LTBGKOAIOJDRJO-UHFFFAOYSA-N 0.000 claims 2
- SNMGZSWKBKSKOG-UHFFFAOYSA-N n-[3-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]phenyl]acetamide Chemical compound C=1C(C=2C=C(NC(C)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 SNMGZSWKBKSKOG-UHFFFAOYSA-N 0.000 claims 2
- NHYKVBHTDZTEKT-UHFFFAOYSA-N n-[6-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C=1C(C=2C=C3SC(NC(C)=O)=NC3=CC=2)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl NHYKVBHTDZTEKT-UHFFFAOYSA-N 0.000 claims 2
- PZWGBZLUHRRULA-UHFFFAOYSA-N n-[[2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=NO)C(F)=CC=2)=NC(OC)=N1 PZWGBZLUHRRULA-UHFFFAOYSA-N 0.000 claims 2
- UOWHSPCVEWDCAX-UHFFFAOYSA-N n-[[2-methoxy-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=NO)C(OC)=CC=2)=NC(OC)=N1 UOWHSPCVEWDCAX-UHFFFAOYSA-N 0.000 claims 2
- VMYBFTCYLWSGCC-UHFFFAOYSA-N n-ethyl-3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]benzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 VMYBFTCYLWSGCC-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229960002052 salbutamol Drugs 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- RMTQEEYHUNGCDX-UHFFFAOYSA-N 1-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]cyclopentane-1-carboxylic acid Chemical compound C=1C(C=2C=C(C=CC=2)C2(CCCC2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl RMTQEEYHUNGCDX-UHFFFAOYSA-N 0.000 claims 1
- QEEHWPMFRRIVNR-UHFFFAOYSA-N 1-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C2(CCCC2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl QEEHWPMFRRIVNR-UHFFFAOYSA-N 0.000 claims 1
- BMGFBNWIPWZZBK-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate Chemical compound CCOC(=O)OC(C)OC(=O)C(C)(C)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 BMGFBNWIPWZZBK-UHFFFAOYSA-N 0.000 claims 1
- FMIIBDBHCSCYTK-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)OC(C)OC(=O)C(C)(C)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 FMIIBDBHCSCYTK-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- YOOOVGXUWHZYPY-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)OCCN(C)C)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl YOOOVGXUWHZYPY-UHFFFAOYSA-N 0.000 claims 1
- JHGLBFCMHHUEHY-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2-methylpropanoate;dihydrochloride Chemical compound Cl.Cl.C=1C(C=2C=C(C=CC=2)C(C)(C)C(=O)OCCN(C)C)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl JHGLBFCMHHUEHY-UHFFFAOYSA-N 0.000 claims 1
- MCHVLCWZUONPGC-UHFFFAOYSA-N 2-[3-[6-(1-benzothiophen-2-ylmethylamino)-2-methylpyrimidin-4-yl]phenyl]-2-methylpropanoic acid Chemical compound N=1C(C)=NC(NCC=2SC3=CC=CC=C3C=2)=CC=1C1=CC=CC(C(C)(C)C(O)=O)=C1 MCHVLCWZUONPGC-UHFFFAOYSA-N 0.000 claims 1
- AWZWXWUFDXJWRX-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-4-fluorophenyl]-2-methylpropanoic acid Chemical compound C=1C(C=2C(=CC=C(C=2)C(C)(C)C(O)=O)F)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl AWZWXWUFDXJWRX-UHFFFAOYSA-N 0.000 claims 1
- DUJBZAUDHDYEFL-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-4-fluorophenyl]-2-methylpropanoic acid;hydrochloride Chemical compound Cl.C=1C(C=2C(=CC=C(C=2)C(C)(C)C(O)=O)F)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl DUJBZAUDHDYEFL-UHFFFAOYSA-N 0.000 claims 1
- COARABAGVVBZIU-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-2,2-difluoroacetamide Chemical compound C=1C(C=2C=C(C=CC=2)C(F)(F)C(N)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl COARABAGVVBZIU-UHFFFAOYSA-N 0.000 claims 1
- QVMKLRABZHUHMS-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]-n-ethylsulfonyl-2,2-difluoroacetamide Chemical compound CCS(=O)(=O)NC(=O)C(F)(F)C1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC(Cl)=CC=3)Cl)C=2)=C1 QVMKLRABZHUHMS-UHFFFAOYSA-N 0.000 claims 1
- BECJKMCLZUNZHB-UHFFFAOYSA-N 2-[3-[6-[2-(2,4-dichlorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenyl]propanoic acid Chemical compound C=1C(C=2C=C(C=CC=2)C(C)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(Cl)C=C1Cl BECJKMCLZUNZHB-UHFFFAOYSA-N 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- ARDIRBNLHABHGM-UHFFFAOYSA-N 2-chloro-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(Cl)=CC=2)C(O)=O)=NC(OC)=N1 ARDIRBNLHABHGM-UHFFFAOYSA-N 0.000 claims 1
- OMHGGYUHFYFPEC-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(2-pyridin-3-ylethyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=NC=CC=3)C=2)=C1 OMHGGYUHFYFPEC-UHFFFAOYSA-N 0.000 claims 1
- JGCBAUJILOCTAF-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(2-pyridin-3-ylethyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=NC=CC=3)C=2)=C1 JGCBAUJILOCTAF-UHFFFAOYSA-N 0.000 claims 1
- BVSYBFDWTZTWOO-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(2-thiophen-2-ylethyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3SC=CC=3)C=2)=C1 BVSYBFDWTZTWOO-UHFFFAOYSA-N 0.000 claims 1
- LRMIVWNHYFZDGV-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(2-thiophen-2-ylethyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3SC=CC=3)C=2)=C1 LRMIVWNHYFZDGV-UHFFFAOYSA-N 0.000 claims 1
- QLWRBRAPKLHSNJ-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(3-phenylpropyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCCC=3C=CC=CC=3)C=2)=C1 QLWRBRAPKLHSNJ-UHFFFAOYSA-N 0.000 claims 1
- ASDVREIZZWMZAC-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-(3-phenylpropyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCCC=3C=CC=CC=3)C=2)=C1 ASDVREIZZWMZAC-UHFFFAOYSA-N 0.000 claims 1
- HARSJXFCKXJFOF-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[(4-methoxyphenyl)methyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC(C=2C=C(OC)C=CC=2)=NC(OC)=N1 HARSJXFCKXJFOF-UHFFFAOYSA-N 0.000 claims 1
- NZKCFPCTILTOHJ-UHFFFAOYSA-N 2-methoxy-6-(3-methoxyphenyl)-n-[(4-methoxyphenyl)methyl]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CNC1=CC(C=2C=C(OC)C=CC=2)=NC(OC)=N1 NZKCFPCTILTOHJ-UHFFFAOYSA-N 0.000 claims 1
- HIXLPEPAQPRNNN-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[(2-methoxyphenyl)methoxy]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(OCC=2C(=CC=CC=2)OC)=NC(OC)=N1 HIXLPEPAQPRNNN-UHFFFAOYSA-N 0.000 claims 1
- HUYDFUJLZGNIOQ-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[(2-methoxyphenyl)methoxy]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(OCC=2C(=CC=CC=2)OC)=NC(OC)=N1 HUYDFUJLZGNIOQ-UHFFFAOYSA-N 0.000 claims 1
- GKFUFVDESUEZDR-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(2h-tetrazol-5-ylmethyl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CC=3NN=NN=3)C=CC=2)=NC(OC)=N1 GKFUFVDESUEZDR-UHFFFAOYSA-N 0.000 claims 1
- YOINIBCPZUCCGG-UHFFFAOYSA-N 2-methoxy-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]-6-(3-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C4=CC(OC)=CC=C4NC=3)C=2)=C1 YOINIBCPZUCCGG-UHFFFAOYSA-N 0.000 claims 1
- YMDVMUGHFPYNSE-UHFFFAOYSA-N 2-methoxy-n-[2-(5-methoxy-1h-indol-3-yl)ethyl]-6-(3-methoxyphenyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C4=CC(OC)=CC=C4NC=3)C=2)=C1 YMDVMUGHFPYNSE-UHFFFAOYSA-N 0.000 claims 1
- MWDNXBVPIDBXKP-UHFFFAOYSA-N 2-methoxy-n-[2-(6-methoxy-1h-indol-3-yl)ethyl]-6-(3-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C4=CC=C(OC)C=C4NC=3)C=2)=C1 MWDNXBVPIDBXKP-UHFFFAOYSA-N 0.000 claims 1
- JOPBKSIEBSDVHM-UHFFFAOYSA-N 2-methoxy-n-[2-(6-methoxy-1h-indol-3-yl)ethyl]-6-(3-methoxyphenyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C4=CC=C(OC)C=C4NC=3)C=2)=C1 JOPBKSIEBSDVHM-UHFFFAOYSA-N 0.000 claims 1
- IRBGXAORPALMRO-UHFFFAOYSA-N 3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenol Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(O)C=CC=2)=NC(OC)=N1 IRBGXAORPALMRO-UHFFFAOYSA-N 0.000 claims 1
- WFXFELUPJRESPC-UHFFFAOYSA-N 3-[6-[2-(4-chlorophenyl)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=C1 WFXFELUPJRESPC-UHFFFAOYSA-N 0.000 claims 1
- LBIRNDRPXBNNQA-UHFFFAOYSA-N 3-[6-[2-(4-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=CC=C(F)C=C1 LBIRNDRPXBNNQA-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- BSLUBTJMDPVQBG-UHFFFAOYSA-N 4-[2-[[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methylamino]ethyl]phenol Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CNCCC=3C=CC(O)=CC=3)C=CC=2)=NC(OC)=N1 BSLUBTJMDPVQBG-UHFFFAOYSA-N 0.000 claims 1
- GJOWCWHPHBWFOH-UHFFFAOYSA-N 4-[2-[[3-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methylamino]ethyl]phenol;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CNCCC=3C=CC(O)=CC=3)C=CC=2)=NC(OC)=N1 GJOWCWHPHBWFOH-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- JAEOASXMHNSBPU-UHFFFAOYSA-N 5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]-n-methylthiophene-2-carboxamide Chemical compound S1C(C(=O)NC)=CC=C1C1=CC(NCCC=2C=CC(OC)=CC=2)=NC(OC)=N1 JAEOASXMHNSBPU-UHFFFAOYSA-N 0.000 claims 1
- DDMKGICGMQRLFF-UHFFFAOYSA-N 5-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=1C(C=2C=C3CC(OC3=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 DDMKGICGMQRLFF-UHFFFAOYSA-N 0.000 claims 1
- PXURFLLZIYUXHG-UHFFFAOYSA-N 5-[2-methoxy-6-[2-[4-(trifluoromethoxy)phenyl]ethylamino]pyrimidin-4-yl]-2,3-dihydro-1-benzofuran-2-carboxylic acid;hydrochloride Chemical compound Cl.C=1C(C=2C=C3CC(OC3=CC=2)C(O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)(F)F)C=C1 PXURFLLZIYUXHG-UHFFFAOYSA-N 0.000 claims 1
- ZLFBUABOLIOZNL-UHFFFAOYSA-N 6-(1h-indol-6-yl)-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C3NC=CC3=CC=2)=NC(OC)=N1 ZLFBUABOLIOZNL-UHFFFAOYSA-N 0.000 claims 1
- HAPGMWPOTFYQBK-UHFFFAOYSA-N 6-[3-(aminomethyl)-4-fluorophenyl]-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CN)C(F)=CC=2)=NC(OC)=N1 HAPGMWPOTFYQBK-UHFFFAOYSA-N 0.000 claims 1
- CUAUEBQSFHWKMK-UHFFFAOYSA-N 6-[3-(aminomethyl)-4-fluorophenyl]-2-methoxy-n-[2-(4-methoxyphenyl)ethyl]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CN)C(F)=CC=2)=NC(OC)=N1 CUAUEBQSFHWKMK-UHFFFAOYSA-N 0.000 claims 1
- RGEYUXIBVOBARX-UHFFFAOYSA-N C(C)S(=O)(=O)O.ClC1=C(C=CC(=C1)Cl)CCNC1=CC(=NC(=N1)OC)C=1C=C(C=CC1)C(C(=O)O)(F)F Chemical compound C(C)S(=O)(=O)O.ClC1=C(C=CC(=C1)Cl)CCNC1=CC(=NC(=N1)OC)C=1C=C(C=CC1)C(C(=O)O)(F)F RGEYUXIBVOBARX-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical group CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 229960003592 fexofenadine Drugs 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 125000004250 isochroman-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])OC2([H])* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 229960003088 loratadine Drugs 0.000 claims 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960005127 montelukast Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- ZOSSSBOOQDNQHG-UHFFFAOYSA-N n-[2-(2,2-difluoro-1,3-benzodioxol-5-yl)ethyl]-2-methoxy-6-pyridin-3-ylpyrimidin-4-amine;hydrochloride Chemical compound Cl.N=1C(OC)=NC(NCCC=2C=C3OC(F)(F)OC3=CC=2)=CC=1C1=CC=CN=C1 ZOSSSBOOQDNQHG-UHFFFAOYSA-N 0.000 claims 1
- LTBVBIPAORHECL-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-6-[3-[2-(2h-tetrazol-5-yl)propan-2-yl]phenyl]pyrimidin-4-amine Chemical compound C=1C(C=2C=C(C=CC=2)C(C)(C)C2=NNN=N2)=NC(C)=NC=1NCCC1=CC=C(Cl)C=C1Cl LTBVBIPAORHECL-UHFFFAOYSA-N 0.000 claims 1
- ZTFMGVAXPOKLSG-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-6-[3-[2-(2h-tetrazol-5-yl)propan-2-yl]phenyl]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)C(C)(C)C=2NN=NN=2)=NC(C)=NC=1NCCC1=CC=C(Cl)C=C1Cl ZTFMGVAXPOKLSG-UHFFFAOYSA-N 0.000 claims 1
- PXUDKWPUOMDDEY-UHFFFAOYSA-N n-[2-(2-chloro-6-fluorophenyl)ethyl]-2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC=CC=3F)Cl)C=2)=C1 PXUDKWPUOMDDEY-UHFFFAOYSA-N 0.000 claims 1
- RSOBODCJRXCVKB-UHFFFAOYSA-N n-[2-(2-chloro-6-fluorophenyl)ethyl]-2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C(=CC=CC=3F)Cl)C=2)=C1 RSOBODCJRXCVKB-UHFFFAOYSA-N 0.000 claims 1
- JYHSGCATSUYCIZ-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-methoxy-6-(3-methoxyphenyl)pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(OC)N=C(NCCC=3C=CC(N)=CC=3)C=2)=C1 JYHSGCATSUYCIZ-UHFFFAOYSA-N 0.000 claims 1
- QWDRNSWMZBLJHE-UHFFFAOYSA-N n-[2-[3-[6-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]phenyl]ethyl]acetamide Chemical compound C=1C(C=2C=C(CCNC(C)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(C(F)(F)F)C=C1F QWDRNSWMZBLJHE-UHFFFAOYSA-N 0.000 claims 1
- IKWQIIGXSKAHLO-UHFFFAOYSA-N n-[2-[3-[6-[2-[2-fluoro-4-(trifluoromethyl)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]phenyl]ethyl]acetamide;hydrochloride Chemical compound Cl.C=1C(C=2C=C(CCNC(C)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(C(F)(F)F)C=C1F IKWQIIGXSKAHLO-UHFFFAOYSA-N 0.000 claims 1
- UHXSNAOXVDXCOT-UHFFFAOYSA-N n-[2-[4-(difluoromethoxy)phenyl]ethyl]-2-methoxy-6-(3-methylsulfonylphenyl)pyrimidin-4-amine Chemical compound C=1C(C=2C=C(C=CC=2)S(C)(=O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)F)C=C1 UHXSNAOXVDXCOT-UHFFFAOYSA-N 0.000 claims 1
- RCSAPWDDVKQCRL-UHFFFAOYSA-N n-[2-[4-(difluoromethoxy)phenyl]ethyl]-2-methoxy-6-(3-methylsulfonylphenyl)pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C(C=2C=C(C=CC=2)S(C)(=O)=O)=NC(OC)=NC=1NCCC1=CC=C(OC(F)F)C=C1 RCSAPWDDVKQCRL-UHFFFAOYSA-N 0.000 claims 1
- ZRRMHLLPVKQVCP-UHFFFAOYSA-N n-[3-[6-[2-[4-(difluoromethoxy)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]phenyl]acetamide Chemical compound C=1C(C=2C=C(NC(C)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(OC(F)F)C=C1 ZRRMHLLPVKQVCP-UHFFFAOYSA-N 0.000 claims 1
- WJBZNOMGUKCJQW-UHFFFAOYSA-N n-[3-[6-[2-[4-(difluoromethoxy)phenyl]ethylamino]-2-methoxypyrimidin-4-yl]phenyl]acetamide;hydrochloride Chemical compound Cl.C=1C(C=2C=C(NC(C)=O)C=CC=2)=NC(OC)=NC=1NCCC1=CC=C(OC(F)F)C=C1 WJBZNOMGUKCJQW-UHFFFAOYSA-N 0.000 claims 1
- MSYMKNWKLDCUJM-UHFFFAOYSA-N n-[[2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methyl]-2-methoxyacetamide Chemical compound C1=C(F)C(CNC(=O)COC)=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 MSYMKNWKLDCUJM-UHFFFAOYSA-N 0.000 claims 1
- FQWIVTWNWXACIU-UHFFFAOYSA-N n-[[2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methyl]-2-methoxyacetamide;hydrochloride Chemical compound Cl.C1=C(F)C(CNC(=O)COC)=CC(C=2N=C(OC)N=C(NCCC=3C=CC(OC)=CC=3)C=2)=C1 FQWIVTWNWXACIU-UHFFFAOYSA-N 0.000 claims 1
- VCXHYAPBPBZGLT-UHFFFAOYSA-N n-[[2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CNCCN(C)C)C(F)=CC=2)=NC(OC)=N1 VCXHYAPBPBZGLT-UHFFFAOYSA-N 0.000 claims 1
- HNYPPIBKEOOZEA-UHFFFAOYSA-N n-[[2-fluoro-5-[2-methoxy-6-[2-(4-methoxyphenyl)ethylamino]pyrimidin-4-yl]phenyl]methyl]-n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(CNCCN(C)C)C(F)=CC=2)=NC(OC)=N1 HNYPPIBKEOOZEA-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical group FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 claims 1
- 229960002586 roflumilast Drugs 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 229960000195 terbutaline Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 229960004764 zafirlukast Drugs 0.000 claims 1
- 0 O=C1OC(C(**I)*C2CCC2)=NN1 Chemical compound O=C1OC(C(**I)*C2CCC2)=NN1 0.000 description 4
- GITAXXBPKUZBDM-UHFFFAOYSA-N C=[Cl]N1CCOCC1 Chemical compound C=[Cl]N1CCOCC1 GITAXXBPKUZBDM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61927204P | 2004-10-15 | 2004-10-15 | |
| US60/619,272 | 2004-10-15 | ||
| PCT/US2005/037148 WO2006044732A2 (en) | 2004-10-15 | 2005-10-14 | 2, 6-substituted-4-monosubstitutedamino-pyrimidine as prostaglandin d2 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008516974A JP2008516974A (ja) | 2008-05-22 |
| JP2008516974A5 true JP2008516974A5 (enExample) | 2008-07-31 |
| JP4970274B2 JP4970274B2 (ja) | 2012-07-04 |
Family
ID=36072155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007536972A Expired - Fee Related JP4970274B2 (ja) | 2004-10-15 | 2005-10-14 | プロスタグランジンｄ２受容体アンタゴニストとしての２，６−置換−４−一置換アミノ−ピリミジン |
Country Status (35)
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200600457A (es) * | 2005-10-13 | 2007-04-27 | Aventis Pharma Inc | Sal de fosfato dihidrogeno como antagonistas del receptor de prostaglandina d2 |
| DOP2007000068A (es) * | 2006-04-12 | 2007-10-31 | Sanofi Aventis Us Llc | Compuestos de amino-pirimidina 2,6-sustituidos-4-monosustituidos como antagonistas del receptor de prostaglandina d2 |
| WO2008039882A1 (en) * | 2006-09-30 | 2008-04-03 | Sanofi-Aventis U.S. Llc | A combination of niacin and a prostaglandin d2 receptor antagonist |
| NZ579892A (en) * | 2007-03-30 | 2012-03-30 | Sanofi Aventis | Pyrimidine hydrazide compounds as prostaglandin D synthase inhibitors |
| BRPI0810719A8 (pt) * | 2007-04-30 | 2016-03-08 | Abbott Lab | Inibidores da enzima diacilglicerol o-acetiltansferase tipo 1 |
| EP2014657A1 (de) * | 2007-06-21 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Diaminopyrimidine als Modulatoren des EP2-Rezeptors |
| ATE531699T1 (de) | 2007-06-29 | 2011-11-15 | Sanofi Sa | Verfahren zur herstellung von 2-(3-ä6-ä2-(2,4- |
| US7928140B2 (en) | 2007-08-02 | 2011-04-19 | Amgen Inc. | Benzothiazole PI3 kinase modulators for cancer treatment |
| WO2009055730A1 (en) * | 2007-10-25 | 2009-04-30 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| MX2010005033A (es) * | 2007-11-06 | 2010-05-27 | Du Pont | Aminas heterociclicas fungicidas. |
| US7820665B2 (en) | 2007-12-19 | 2010-10-26 | Amgen Inc. | Imidazopyridazine inhibitors of PI3 kinase for cancer treatment |
| WO2009086277A1 (en) | 2007-12-20 | 2009-07-09 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| EP2254415B1 (en) | 2008-02-19 | 2013-01-23 | Janssen Pharmaceutica, N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| US20110053949A1 (en) * | 2008-04-17 | 2011-03-03 | Pfizer Inc. | 4-[3-(aryloxy)benzylidene]-3-methyl piperidine aryl carboxamide compounds useful as faah inhibitors |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| AR074199A1 (es) | 2008-11-20 | 2010-12-29 | Glaxosmithkline Llc | Compuesto de 6-(4-pirimidinil)-1h-indazol, composiciones farmaceuticas que lo comprenden y su uso para preparar un medicamento util para el tratamiento o disminucion de la gravedad del cancer. |
| AR074776A1 (es) * | 2008-12-18 | 2011-02-09 | Sanofi Aventis | Metodo para tratar la degeneracion macular; modulando el sistema inmunitario del paciente |
| WO2011022348A1 (en) | 2009-08-18 | 2011-02-24 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid amide hydrolase |
| MX2012010038A (es) | 2010-03-16 | 2012-10-01 | Aventis Pharma Inc | Una pirimidina sustituida como un antagonista del receptor de la prostaglandina d2. |
| CA2793223A1 (en) * | 2010-03-16 | 2011-09-22 | Aventis Pharmaceuticals Inc. | Substituted pyrimidines as prostaglandin d2 receptor antagonists |
| UY33304A (es) * | 2010-04-02 | 2011-10-31 | Amgen Inc | Compuestos heterocíclicos y sus usos |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
| CA2805452C (en) | 2010-07-05 | 2018-07-31 | Actelion Pharmaceuticals Ltd | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2621276B1 (en) * | 2010-09-30 | 2017-12-27 | Merck Sharp & Dohme Corp. | 2-alkoxy pyrimidine pde10 inhibitors |
| PH12013502516A1 (en) * | 2011-06-06 | 2017-08-23 | Chiesi Farm Spa | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
| PE20141371A1 (es) | 2011-08-29 | 2014-10-13 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos |
| FR2983859B1 (fr) | 2011-12-12 | 2014-01-17 | Sanofi Sa | Derives de 1,3,5-triazine-2-amine, leur preparation et leur application en diagnostique et en therapeutique |
| TW201331179A (zh) | 2011-12-21 | 2013-08-01 | Actelion Pharmaceuticals Ltd | 雜環衍生物及其作為前列腺素ｄ２受體調節劑之用途 |
| WO2013134562A1 (en) | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| SG11201406584TA (en) | 2012-04-24 | 2014-11-27 | Vertex Pharma | Dna-pk inhibitors |
| EP2885307A1 (en) | 2012-07-05 | 2015-06-24 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2912458B1 (en) | 2012-10-24 | 2018-07-18 | NYU Winthrop Hospital | Non-invasive biomarker to identify subjects at risk of preterm delivery |
| MX376108B (es) | 2012-12-20 | 2025-03-07 | Tempest Therapeutics Inc | Compuestos de triazolona y usos de los mismos. |
| RS62649B1 (sr) | 2013-03-12 | 2021-12-31 | Vertex Pharma | Inhibitori dnk-pk |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| AU2014315151A1 (en) | 2013-09-06 | 2016-03-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| KR102411227B1 (ko) | 2013-10-17 | 2022-06-21 | 버텍스 파마슈티칼스 인코포레이티드 | Dna-pk 억제제로서 (s)-n-메틸-8-(1-((2'-메틸-[4,5'-비피리미딘]-6-일)아미노)프로판-2-일)퀴놀린-4-카복스아미드 및 이의 듀테로화된 유도체의 공결정 |
| JP2018123058A (ja) * | 2015-06-08 | 2018-08-09 | 石原産業株式会社 | ジフルオロメチレン化合物 |
| CN109734651A (zh) * | 2015-07-06 | 2019-05-10 | 江苏恩华药业股份有限公司 | 阿芬太尼、舒芬太尼的制备方法及用于制备阿芬太尼、舒芬太尼的化合物 |
| US10329277B2 (en) * | 2015-07-16 | 2019-06-25 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(3-methyl-2-OXO-2,3-dihydro-1h-benzo[d]imidazol-1-yl)pyrimidin-2-yl)amino)phenyl)acrylamide hydrochloride as an inhibitor of epidermal growth factor receptor activity |
| CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
| MX394860B (es) | 2016-09-27 | 2025-03-24 | Vertex Pharma | Metodo para tratar cancer usando una combinacion de agentes que dañan adn e inhibidores de proteina cinasa dependiente de adn (adn-pk). |
| WO2018107158A1 (en) * | 2016-12-09 | 2018-06-14 | Celtaxsys, Inc. | Monamine and monoamine derivatives as inhibitors of leukotriene a4 hydrolase |
| PE20191787A1 (es) | 2017-05-18 | 2019-12-24 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituidos |
| US11325899B2 (en) | 2017-05-18 | 2022-05-10 | Idorsia Pharmaceuticals Ltd | Benzofurane and benzothiophene derivatives as PGE2 receptor modulators |
| AR111808A1 (es) | 2017-05-18 | 2019-08-21 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| EA201992676A1 (ru) | 2017-05-18 | 2020-05-06 | Идорсия Фармасьютиклз Лтд | Фенильные производные в качестве модуляторов pge2 рецепторов |
| KR102612140B1 (ko) | 2017-05-18 | 2023-12-08 | 이도르시아 파마슈티컬스 리미티드 | 피리미딘 유도체 |
| KR20200109293A (ko) | 2017-09-13 | 2020-09-22 | 프로제너티, 인크. | 자간전증 바이오마커 및 관련된 시스템 및 방법 |
| JP2021510153A (ja) | 2018-01-05 | 2021-04-15 | アイカーン スクール オブ メディシン アット マウント サイナイ | 膵臓ベータ細胞の増殖を増加させる方法、治療方法、および組成物 |
| ES3038913T3 (en) | 2018-03-20 | 2025-10-15 | Icahn School Med Mount Sinai | Beta-carboline derivatives as dyrk1a inhibitors for the treatment of e.g. diabetes |
| GB201807898D0 (en) * | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
| CA3124353A1 (en) * | 2018-12-31 | 2020-07-09 | Icahn School Of Medicine At Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
| CN110642880B (zh) * | 2019-10-11 | 2021-12-31 | 长沙麓兴生物科技有限公司 | 一种氮未取代吡唑和吲唑类硼酸的制备方法 |
| WO2021113710A1 (en) | 2019-12-04 | 2021-06-10 | Progenity, Inc. | Assessment of preeclampsia using assays for free and dissociated placental growth factor |
| JP2023539113A (ja) * | 2020-08-18 | 2023-09-13 | サイビン アイアールエル リミテッド | フェネチルアミン誘導体、組成物およびその使用方法 |
| CN116507611A (zh) * | 2020-11-06 | 2023-07-28 | 佩勒梅德有限公司 | 新型衣壳组装抑制剂 |
| CN117599052B (zh) * | 2023-07-25 | 2026-07-24 | 温州医科大学附属眼视光医院 | Ptgds的抑制剂在制备治疗白内障药物上的应用 |
| US12220411B1 (en) | 2023-07-25 | 2025-02-11 | The Eye Hospital Of Wenzhou Medical University | Application of PTGDS inhibitor in preparation of drug for treating cataracts |
| TW202604507A (zh) | 2024-05-02 | 2026-02-01 | 瑞士商愛杜西亞製藥有限公司 | 經n-取代之吲哚衍生物的結晶形式 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH499528A (de) * | 1965-10-22 | 1970-11-30 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Pyrimidine |
| GB1143167A (en) * | 1967-01-25 | 1969-02-19 | Ucb Sa | Derivatives of pyrimidine |
| DE4031798A1 (de) * | 1990-10-08 | 1992-04-09 | Hoechst Ag | Pyridylpyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| DE4031792A1 (de) * | 1990-10-08 | 1991-04-25 | Franz Reiner Dipl Phy Thedieck | Indikator-element aus festen bestandteilen |
| FR2753378B1 (fr) * | 1996-09-17 | 1998-11-20 | Oreal | Utilisation dans une composition en tant que stimulateur de tyrosinase d'au moins un derive de pyrimidine 3-oxyde, substitue en 6 |
| US6169086B1 (en) * | 1997-01-27 | 2001-01-02 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivatives |
| GB9806739D0 (en) * | 1998-03-28 | 1998-05-27 | Univ Newcastle Ventures Ltd | Cyclin dependent kinase inhibitors |
| ATE250053T1 (de) * | 1999-07-15 | 2003-10-15 | Pharmacopeia Inc | Bradikinin b1 rezeptor antagonisten |
| DE10006453A1 (de) | 2000-02-14 | 2001-08-16 | Bayer Ag | Piperidylcarbonsäuren als Integrinantagonisten |
| US6410583B1 (en) * | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
| WO2002092090A1 (en) * | 2001-05-14 | 2002-11-21 | Bristol-Myers Squibb Pharma Company | Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands |
| US20030208067A1 (en) * | 2001-05-30 | 2003-11-06 | Cao Sheldon Xiaodong | Inhibitors of protein kinase for the treatment of disease |
| CA2463563A1 (en) * | 2001-10-12 | 2003-04-17 | Irm Llc | Kinase inhibitor scaffolds and methods for their preparation |
| AR038136A1 (es) * | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
| WO2004017920A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
| AU2003265663A1 (en) | 2002-08-23 | 2004-03-11 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| US20070155701A1 (en) * | 2002-08-23 | 2007-07-05 | Alexandros Makriyannis | Keto cannabinoids with therapeutic indications |
| CA2505361A1 (en) * | 2002-11-11 | 2004-05-27 | Bayer Healthcare Ag | Phenyl or heteroaryl amino alkane derivatives as ip receptor antagonist |
| KR20060052806A (ko) * | 2003-07-25 | 2006-05-19 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 항균제로서 치환된 2,4-비스(알킬아미노)피리미딘 또는-퀴나졸린의 용도 |
| AU2005225471B2 (en) * | 2004-03-26 | 2011-05-12 | Methylgene Inc. | Inhibitors of histone deacetylase |
| ES2364340T3 (es) * | 2004-03-30 | 2011-08-31 | Vertex Pharmaceuticals Incorporated | Azaindoles útiles como inhibidores de jak y otras proteína quinasas. |
| EP1805142A4 (en) * | 2004-09-23 | 2009-06-10 | Reddy Us Therapeutics Inc | PYRIDINE-BASED COMPOUNDS, PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING SAME |
| AU2005309566A1 (en) * | 2004-11-22 | 2006-06-01 | Vertex Pharmaceuticals Incorporated | Bicyclic inhibitors or Rho kinase |
| 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
- 2005-10-13 HN HN2005000795A patent/HN2005000795A/es unknown
- 2005-10-13 GT GT200500284A patent/GT200500284A/es unknown
- 2005-10-14 JP JP2007536972A patent/JP4970274B2/ja not_active Expired - Fee Related
- 2005-10-14 MY MYPI2010000586A patent/MY157036A/en unknown
- 2005-10-14 EP EP05812481A patent/EP1891019B1/en not_active Expired - Lifetime
- 2005-10-14 PE PE2005001214A patent/PE20060936A1/es not_active Application Discontinuation
- 2005-10-14 UY UY29167A patent/UY29167A1/es unknown
- 2005-10-14 PA PA20058649801A patent/PA8649801A1/es unknown
- 2005-10-14 MX MX2007003155A patent/MX2007003155A/es active IP Right Grant
- 2005-10-14 ES ES05812481T patent/ES2392091T3/es not_active Expired - Lifetime
- 2005-10-14 SI SI200531599T patent/SI1891019T1/sl unknown
- 2005-10-14 NZ NZ553919A patent/NZ553919A/en not_active IP Right Cessation
- 2005-10-14 PL PL05812481T patent/PL1891019T3/pl unknown
- 2005-10-14 CN CN2005800353962A patent/CN101039920B/zh not_active Expired - Fee Related
- 2005-10-14 TW TW094135790A patent/TWI372751B/zh not_active IP Right Cessation
- 2005-10-14 KR KR1020077011039A patent/KR101280268B1/ko not_active Expired - Fee Related
- 2005-10-14 UA UAA200705281A patent/UA88485C2/ru unknown
- 2005-10-14 SV SV2005002272A patent/SV2006002272A/es unknown
- 2005-10-14 DK DK05812481.9T patent/DK1891019T3/da active
- 2005-10-14 RU RU2007117913/04A patent/RU2417990C2/ru not_active IP Right Cessation
- 2005-10-14 CA CA2583742A patent/CA2583742C/en not_active Expired - Fee Related
- 2005-10-14 AR ARP050104318A patent/AR053770A1/es unknown
- 2005-10-14 AU AU2005295502A patent/AU2005295502B2/en not_active Ceased
- 2005-10-14 PT PT05812481T patent/PT1891019E/pt unknown
- 2005-10-14 BR BRPI0516482-6A patent/BRPI0516482A/pt not_active Application Discontinuation
- 2005-10-14 WO PCT/US2005/037148 patent/WO2006044732A2/en not_active Ceased
- 2005-10-14 MY MYPI20054844A patent/MY142453A/en unknown
- 2005-10-14 SG SG200906939-4A patent/SG156653A1/en unknown
-
2007
- 2007-03-16 ZA ZA200702209A patent/ZA200702209B/xx unknown
- 2007-03-16 TN TNP2007000098A patent/TNSN07098A1/en unknown
- 2007-03-20 CR CR9003A patent/CR9003A/es not_active Application Discontinuation
- 2007-03-21 IL IL182090A patent/IL182090A/en not_active IP Right Cessation
- 2007-04-13 EC EC2007007398A patent/ECSP077398A/es unknown
- 2007-04-16 US US11/735,760 patent/US7517889B2/en not_active Expired - Lifetime
- 2007-04-16 US US11/735,751 patent/US8193183B2/en active Active
- 2007-05-04 MA MA29872A patent/MA29071B1/fr unknown
- 2007-05-11 NO NO20072440A patent/NO339772B1/no not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2583742A1 (en) | 2,6-substituted-4-monosubstituted amino-pyrimidine as prostaglandin d2 receptor antagonists | |
| CN101492416B (zh) | 影响葡糖激酶的化合物 | |
| JP2020516671A5 (enExample) | ||
| US7211594B2 (en) | Indazole compounds and compositions thereof as JNK inhibitors and for the treatment of diseases associated therewith | |
| RU2019132212A (ru) | Селективные ингибиторы hdac6 | |
| RU2012116207A (ru) | Производные индола в качестве модуляторов crac | |
| US9580438B2 (en) | Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and CNS disorders | |
| AU2004266719A1 (en) | Methods of treating COPD and pulmonary hypertension | |
| JP2016522246A5 (enExample) | ||
| JP2005536458A5 (enExample) | ||
| JP2004531473A5 (enExample) | ||
| RU2003118448A (ru) | Производные замещенного триазолдиамина и их применение в качестве ингибиторов киназы | |
| JP2007530690A5 (enExample) | ||
| JP2017537948A5 (enExample) | ||
| JP2010504280A5 (enExample) | ||
| JP2008500336A5 (enExample) | ||
| KR20090087916A (ko) | 4-페닐-6-(2,2,2-트리플루오로-1-페닐에톡시)피리미딘계 화합물 및 그의 사용 방법 | |
| JP2016523976A5 (enExample) | ||
| JP2020520354A5 (enExample) | ||
| JP2014523400A5 (enExample) | ||
| AU2011238616A1 (en) | Multisubstituted aromatic compounds as inhibitors of thrombin | |
| JP2022553351A5 (enExample) | ||
| JP2009541268A5 (enExample) | ||
| US20170107206A1 (en) | Modulators of atp-binding cassette transporters | |
| US20070185163A1 (en) | Imidazol derivatives of piperidine as histamine antagonists |