RU2417990C2 - 2,6-замещенные-4-монозамещенный амино-пиримидины как антагонисты рецептора простагландина d2 - Google Patents
2,6-замещенные-4-монозамещенный амино-пиримидины как антагонисты рецептора простагландина d2 Download PDFInfo
- Publication number
- RU2417990C2 RU2417990C2 RU2007117913/04A RU2007117913A RU2417990C2 RU 2417990 C2 RU2417990 C2 RU 2417990C2 RU 2007117913/04 A RU2007117913/04 A RU 2007117913/04A RU 2007117913 A RU2007117913 A RU 2007117913A RU 2417990 C2 RU2417990 C2 RU 2417990C2
- Authority
- RU
- Russia
- Prior art keywords
- ethylamino
- methoxy
- methoxyphenyl
- methoxypyrimidin
- pyrimidin
- Prior art date
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- 102000009389 Prostaglandin D receptors Human genes 0.000 title claims description 7
- 108050000258 Prostaglandin D receptors Proteins 0.000 title claims description 7
- 229940044551 receptor antagonist Drugs 0.000 title description 4
- 239000002464 receptor antagonist Substances 0.000 title description 4
- 150000005005 aminopyrimidines Chemical class 0.000 title description 3
- -1 cyano, carboxy, hydroxy Chemical group 0.000 claims abstract description 748
- 150000001875 compounds Chemical class 0.000 claims abstract description 302
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 76
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 72
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 59
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 53
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 51
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 46
- 150000002367 halogens Chemical class 0.000 claims abstract description 44
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 230000000172 allergic effect Effects 0.000 claims abstract description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 11
- 229910052727 yttrium Inorganic materials 0.000 claims abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 126
- 125000001424 substituent group Chemical group 0.000 claims description 101
- 150000001204 N-oxides Chemical class 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 84
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 40
- 150000001412 amines Chemical class 0.000 claims description 35
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 29
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 20
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 19
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
- 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 description 14
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 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 description 12
- 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 description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 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 description 11
- 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 description 10
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 10
- 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 description 10
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 10
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 10
- 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 description 9
- 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 description 9
- UVUQVKDHNYUOJX-UHFFFAOYSA-N 2h-oxadiazol-5-one;hydrochloride Chemical compound Cl.O=C1C=NNO1 UVUQVKDHNYUOJX-UHFFFAOYSA-N 0.000 claims description 9
- 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 description 9
- 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 description 9
- 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 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 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 description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
- 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 description 8
- 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 description 8
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 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 description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 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 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- FMTYOWVLLAVBLR-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)CCNC1=CC(=NC(=N1)OC)C=1C=C(C=CC=1)C(C(=O)C(C)S(=O)(=O)N)(C)C Chemical compound ClC1=C(C=CC(=C1)Cl)CCNC1=CC(=NC(=N1)OC)C=1C=C(C=CC=1)C(C(=O)C(C)S(=O)(=O)N)(C)C FMTYOWVLLAVBLR-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
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- 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 description 5
- 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 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
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- 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 description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 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 description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 125000004564 2,3-dihydrobenzofuran-2-yl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- MGAHIHYFRNPDBD-UHFFFAOYSA-N 2-[3-[2-methoxy-6-[2-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]ethylamino]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=1NCCC(C=C1)=CC=C1C1=NN=C(C)O1 MGAHIHYFRNPDBD-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- HYOBTCWGANWIBA-UHFFFAOYSA-N 2-methoxy-n-[2-(4-methoxyphenyl)ethyl]-6-[3-(5-methyl-1h-1,2,4-triazol-3-yl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=CC(C=2C=C(C=CC=2)C=2NN=C(C)N=2)=NC(OC)=N1 HYOBTCWGANWIBA-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- XGNCDUXMJUYPLT-UHFFFAOYSA-N 5-[[5-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]-2-oxopyridin-1-yl]methyl]-3h-1,3,4-oxadiazol-2-one Chemical compound C=1C(C2=CN(CC=3OC(=O)NN=3)C(=O)C=C2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl XGNCDUXMJUYPLT-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 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 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- AGDWTJCIIOKOOH-UHFFFAOYSA-N 3-[[3-[6-[2-(2-chloro-6-fluorophenyl)ethylamino]-2-methoxypyrimidin-4-yl]phenoxy]methyl]-2h-1,2,4-oxadiazol-5-one;hydrochloride Chemical compound Cl.C=1C(C=2C=C(OCC=3NC(=O)ON=3)C=CC=2)=NC(OC)=NC=1NCCC1=C(F)C=CC=C1Cl AGDWTJCIIOKOOH-UHFFFAOYSA-N 0.000 claims description 3
- KIWNCNMFFWACKC-UHFFFAOYSA-N CC(C(C(C1=CC(C2=NC(OC)=NC(NCCC(C=CC(Cl)=C3)=C3Cl)=C2)=CC=C1)(F)F)=O)S(N)(=O)=O Chemical compound CC(C(C(C1=CC(C2=NC(OC)=NC(NCCC(C=CC(Cl)=C3)=C3Cl)=C2)=CC=C1)(F)F)=O)S(N)(=O)=O KIWNCNMFFWACKC-UHFFFAOYSA-N 0.000 claims description 3
- MDRZGPZOQVVRQA-UHFFFAOYSA-N CCN1NCNC1COC1=CC(C2=NC(OC)=NC(NCCC(C=C3)=CC(F)=C3F)=C2)=CC=C1 Chemical compound CCN1NCNC1COC1=CC(C2=NC(OC)=NC(NCCC(C=C3)=CC(F)=C3F)=C2)=CC=C1 MDRZGPZOQVVRQA-UHFFFAOYSA-N 0.000 claims description 3
- NIRDALXROFEBCZ-UHFFFAOYSA-N CN1CCN(CC1)CCC1=C(C(=O)O)C=CC=C1C1=NC(=NC(=C1)NCCC1=C(C=C(C=C1)Cl)Cl)OC Chemical compound CN1CCN(CC1)CCC1=C(C(=O)O)C=CC=C1C1=NC(=NC(=C1)NCCC1=C(C=C(C=C1)Cl)Cl)OC NIRDALXROFEBCZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 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 description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 239000010802 sludge Substances 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
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| RU2734849C2 (ru) * | 2015-07-16 | 2020-10-23 | Чиа Тай Тяньцин Фармасьютикал Груп Ко., Лтд. | Производные анилинпиримидина и их применения |
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