CN1259948A - 6,7－二取代－4－氨基吡啶并[2,3－d]嘧啶化合物 - Google Patents

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Publication number

CN1259948A

CN1259948A CN98806072A CN98806072A CN1259948A CN 1259948 A CN1259948 A CN 1259948A CN 98806072 A CN98806072 A CN 98806072A CN 98806072 A CN98806072 A CN 98806072A CN 1259948 A CN1259948 A CN 1259948A

Authority

CN

China

Prior art keywords

phenyl

amino

methyl

pyrimidine

pyrido

Prior art date

1997-04-16

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.)

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• -1 6,7-disubstituted-4-aminopyrido [2,3-D] pyrimidine compounds Chemical class 0.000 title claims description 837
• 150000001875 compounds Chemical class 0.000 claims abstract description 154
• 125000003118 aryl group Chemical group 0.000 claims abstract description 92
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
• 238000000034 method Methods 0.000 claims abstract description 42
• 238000002360 preparation method Methods 0.000 claims abstract description 16
• 241000124008 Mammalia Species 0.000 claims abstract description 14
• 206010040047 Sepsis Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 201000006474 Brain Ischemia Diseases 0.000 claims abstract description 9
• 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 9
• 206010008118 cerebral infarction Diseases 0.000 claims abstract description 9
• 206010061218 Inflammation Diseases 0.000 claims abstract description 7
• 206010015037 epilepsy Diseases 0.000 claims abstract description 7
• 230000004054 inflammatory process Effects 0.000 claims abstract description 7
• 239000003937 drug carrier Substances 0.000 claims abstract description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 40
• AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims description 33
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 32
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 26
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 25
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 125000002252 acyl group Chemical group 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
• 239000003153 chemical reaction reagent Substances 0.000 claims description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 12
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 12
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
• 239000002585 base Substances 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 150000004820 halides Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 11
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 150000001408 amides Chemical class 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 9
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 9
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 8
• JSJORBSFQSEADC-UHFFFAOYSA-N 6-(4-methylphenyl)-7-(5-nitrothiophen-2-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C([N+]([O-])=O)S1 JSJORBSFQSEADC-UHFFFAOYSA-N 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 208000031225 myocardial ischemia Diseases 0.000 claims description 7
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 6
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 6
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 6
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• AYEKAYFYECOMKD-UHFFFAOYSA-N 6-(3-bromophenyl)-7-[4-(dimethylamino)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CC(Br)=C1 AYEKAYFYECOMKD-UHFFFAOYSA-N 0.000 claims description 5
• SESABXYEJPEPAF-UHFFFAOYSA-N 6-(3-chlorophenyl)-7-[4-(dimethylamino)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CC(Cl)=C1 SESABXYEJPEPAF-UHFFFAOYSA-N 0.000 claims description 5
• GZAXXRAUDHWADA-UHFFFAOYSA-N 6-(3-fluoro-4-methylphenyl)-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=C(F)C(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=CS1 GZAXXRAUDHWADA-UHFFFAOYSA-N 0.000 claims description 5
• SKGNDELMCGFBNW-UHFFFAOYSA-N 6-(4-chlorophenyl)-7-[4-(dimethylamino)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=C(Cl)C=C1 SKGNDELMCGFBNW-UHFFFAOYSA-N 0.000 claims description 5
• DVLBGTRBWWVIHA-UHFFFAOYSA-N 6-(4-methylphenyl)-7-(4-phenylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C(C=2C=CC=CC=2)C=C1 DVLBGTRBWWVIHA-UHFFFAOYSA-N 0.000 claims description 5
• LWJJWCUIWNFIMD-UHFFFAOYSA-N 6-(4-methylphenyl)-7-(4-pyrimidin-5-ylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C(C=2C=NC=NC=2)C=C1 LWJJWCUIWNFIMD-UHFFFAOYSA-N 0.000 claims description 5
• FMCJKBDHGIEHMU-UHFFFAOYSA-N 6-(4-methylphenyl)-7-[4-(2-pyridin-2-ylethenyl)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C(C=C1)=CC=C1C=CC1=CC=CC=N1 FMCJKBDHGIEHMU-UHFFFAOYSA-N 0.000 claims description 5
• VBQQIWVCTLIEBG-UHFFFAOYSA-N 6-(4-methylphenyl)-7-[4-(trifluoromethoxy)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C(OC(F)(F)F)C=C1 VBQQIWVCTLIEBG-UHFFFAOYSA-N 0.000 claims description 5
• XGOQVLJOQCXJBJ-UHFFFAOYSA-N 6-(cyclohexylmethyl)-7-[4-(dimethylamino)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1CC1CCCCC1 XGOQVLJOQCXJBJ-UHFFFAOYSA-N 0.000 claims description 5
• UIERGJMSJNOJMO-UHFFFAOYSA-N 6-[(3-bromophenyl)methyl]-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC(Br)=CC=1CC=1C=C2C(N)=NC=NC2=NC=1C1=CC=CS1 UIERGJMSJNOJMO-UHFFFAOYSA-N 0.000 claims description 5
• YVUNAEMEQFGBJH-UHFFFAOYSA-N 6-[(3-fluorophenyl)methyl]-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC(F)=CC=1CC=1C=C2C(N)=NC=NC2=NC=1C1=CC=CS1 YVUNAEMEQFGBJH-UHFFFAOYSA-N 0.000 claims description 5
• ZNRYWQJEDZQRGQ-UHFFFAOYSA-N 6-[(4-bromophenyl)methyl]-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1CC=1C=C2C(N)=NC=NC2=NC=1C1=CC=CS1 ZNRYWQJEDZQRGQ-UHFFFAOYSA-N 0.000 claims description 5
• YMYVQVOEHLUWHB-UHFFFAOYSA-N 6-[(4-propan-2-ylphenyl)methyl]-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1CC1=CC2=C(N)N=CN=C2N=C1C1=CC=CS1 YMYVQVOEHLUWHB-UHFFFAOYSA-N 0.000 claims description 5
• YLEOEWIGCWPIKB-UHFFFAOYSA-N 6-benzyl-7-[4-(dimethylamino)phenyl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1CC1=CC=CC=C1 YLEOEWIGCWPIKB-UHFFFAOYSA-N 0.000 claims description 5
• OFGTXURSNNZGJA-UHFFFAOYSA-N 6-butyl-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound CCCCC1=CC2=C(N)N=CN=C2N=C1C1=CC=CS1 OFGTXURSNNZGJA-UHFFFAOYSA-N 0.000 claims description 5
• YUNLLPZTVDNFPS-UHFFFAOYSA-N 6-pentyl-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound CCCCCC1=CC2=C(N)N=CN=C2N=C1C1=CC=CS1 YUNLLPZTVDNFPS-UHFFFAOYSA-N 0.000 claims description 5
• CBCWBRJFCGBDQW-UHFFFAOYSA-N 7-(3,5-dichlorophenyl)-6-(4-methylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC(Cl)=CC(Cl)=C1 CBCWBRJFCGBDQW-UHFFFAOYSA-N 0.000 claims description 5
• GHKGPSCOUDCKFA-UHFFFAOYSA-N 7-(3-methoxyphenyl)-6-(4-methylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(C=2C(=CC3=C(N)N=CN=C3N=2)C=2C=CC(C)=CC=2)=C1 GHKGPSCOUDCKFA-UHFFFAOYSA-N 0.000 claims description 5
• SJOIOCWKCMUFTE-UHFFFAOYSA-N 7-(4-butoxyphenyl)-6-(4-methylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OCCCC)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=C(C)C=C1 SJOIOCWKCMUFTE-UHFFFAOYSA-N 0.000 claims description 5
• LOUZSLNNZAHIGH-UHFFFAOYSA-N 7-(4-methoxyphenyl)-6-(3-phenylpropyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=NC2=NC=NC(N)=C2C=C1CCCC1=CC=CC=C1 LOUZSLNNZAHIGH-UHFFFAOYSA-N 0.000 claims description 5
• NXLDDXMRBCORMV-UHFFFAOYSA-N 7-(4-methoxyphenyl)-6-(4-methylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=C(C)C=C1 NXLDDXMRBCORMV-UHFFFAOYSA-N 0.000 claims description 5
• NOIMMUBOIPBZAU-UHFFFAOYSA-N 7-(4-methoxyphenyl)-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CS1 NOIMMUBOIPBZAU-UHFFFAOYSA-N 0.000 claims description 5
• GKRJONNOKMRTIB-UHFFFAOYSA-N 7-(5-nitrothiophen-2-yl)-6-(4-propan-2-ylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C([N+]([O-])=O)S1 GKRJONNOKMRTIB-UHFFFAOYSA-N 0.000 claims description 5
• PLPVTHZVWWMXSP-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(2-methylpropyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound CC(C)CC1=CC2=C(N)N=CN=C2N=C1C1=CC=C(N(C)C)C=C1 PLPVTHZVWWMXSP-UHFFFAOYSA-N 0.000 claims description 5
• KEQLQLBJQHZYQF-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(2-phenylethyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1CCC1=CC=CC=C1 KEQLQLBJQHZYQF-UHFFFAOYSA-N 0.000 claims description 5
• RLAKJZCVKPWPDD-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(3-fluorophenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CC(F)=C1 RLAKJZCVKPWPDD-UHFFFAOYSA-N 0.000 claims description 5
• VMYDETZVFWKUOW-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(3-nitrophenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CC([N+]([O-])=O)=C1 VMYDETZVFWKUOW-UHFFFAOYSA-N 0.000 claims description 5
• XICUWRCHWQOBNS-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(3-phenylpropyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1CCCC1=CC=CC=C1 XICUWRCHWQOBNS-UHFFFAOYSA-N 0.000 claims description 5
• UDDRCSTZBXJPHN-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=C(F)C=C1 UDDRCSTZBXJPHN-UHFFFAOYSA-N 0.000 claims description 5
• JHSRINSHMPCCTR-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(4-methylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=C(C)C=C1 JHSRINSHMPCCTR-UHFFFAOYSA-N 0.000 claims description 5
• VJWDZEXCLTXONM-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-(4-propylphenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CCC)=CC=C1C1=CC2=C(N)N=CN=C2N=C1C1=CC=C(N(C)C)C=C1 VJWDZEXCLTXONM-UHFFFAOYSA-N 0.000 claims description 5
• GKBWGMHGJMOLAZ-UHFFFAOYSA-N 7-[4-(dimethylamino)phenyl]-6-phenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C=C1C1=CC=CC=C1 GKBWGMHGJMOLAZ-UHFFFAOYSA-N 0.000 claims description 5
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
• 229910052783 alkali metal Inorganic materials 0.000 claims description 5
• 150000001340 alkali metals Chemical class 0.000 claims description 5
• 230000036506 anxiety Effects 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 210000004351 coronary vessel Anatomy 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
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