CN1252069A - 5,6,7－三取代的－4－氨基吡啶并[2,3－d]嘧啶化合物 - Google Patents

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Publication number

CN1252069A

CN1252069A CN98804117A CN98804117A CN1252069A CN 1252069 A CN1252069 A CN 1252069A CN 98804117 A CN98804117 A CN 98804117A CN 98804117 A CN98804117 A CN 98804117A CN 1252069 A CN1252069 A CN 1252069A

Authority

CN

China

Prior art keywords

phenyl

amino

pyrido

pyrimidine

group

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 5,6,7-trisubstituted-4-aminopyrido [2,3-d] pyrimidine compounds Chemical class 0.000 title claims description 329
• 150000001875 compounds Chemical class 0.000 claims abstract description 210
• 238000000034 method Methods 0.000 claims abstract description 90
• 238000002360 preparation method Methods 0.000 claims abstract description 31
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 241000124008 Mammalia Species 0.000 claims abstract description 11
• 206010040047 Sepsis 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
• 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 6
• 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 99
• UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 90
• 125000003118 aryl group Chemical group 0.000 claims description 84
• 125000001072 heteroaryl group Chemical group 0.000 claims description 80
• 125000000217 alkyl group Chemical group 0.000 claims description 77
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 54
• 239000000203 mixture Substances 0.000 claims description 41
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• 125000000304 alkynyl group Chemical group 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 31
• 125000003342 alkenyl group Chemical group 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 25
• 239000002904 solvent Substances 0.000 claims description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 238000010992 reflux Methods 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 150000003230 pyrimidines Chemical class 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 238000010438 heat treatment Methods 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 9
• 238000000926 separation method Methods 0.000 claims description 9
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000001246 bromo group Chemical group Br* 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• 230000015572 biosynthetic process Effects 0.000 claims description 7
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 claims description 7
• 238000012545 processing Methods 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 7
• JKSIXVZIFHKAPJ-UHFFFAOYSA-N 2h-benzotriazole;hydrate Chemical compound O.C1=CC=C2NN=NC2=C1 JKSIXVZIFHKAPJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 150000003863 ammonium salts Chemical class 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 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 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• HSYOVYMEIHEOMC-UHFFFAOYSA-N 5-(3-bromophenyl)-6-(4-fluorophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(F)C=CC=1C=1C(C=2C=C(Br)C=CC=2)=C2C(N)=NC=NC2=NC=1C(C=N1)=CC=C1N1CCOCC1 HSYOVYMEIHEOMC-UHFFFAOYSA-N 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 4
• RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 4
• ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• XOWWLXDEDLIVTD-UHFFFAOYSA-N 5-(3-bromophenyl)-6-ethyl-7-thiophen-2-ylpyrido[2,3-d]pyrimidin-4-amine Chemical compound CCC1=C(C=2SC=CC=2)N=C2N=CN=C(N)C2=C1C1=CC=CC(Br)=C1 XOWWLXDEDLIVTD-UHFFFAOYSA-N 0.000 claims description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 206010008190 Cerebrovascular accident Diseases 0.000 claims description 3
• 206010014523 Embolism and thrombosis Diseases 0.000 claims description 3
• 206010062016 Immunosuppression Diseases 0.000 claims description 3
• 206010039361 Sacroiliitis Diseases 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• 238000002399 angioplasty Methods 0.000 claims description 3
• 210000004351 coronary vessel Anatomy 0.000 claims description 3
• 150000001924 cycloalkanes Chemical class 0.000 claims description 3
• 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 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 230000007160 gastrointestinal dysfunction Effects 0.000 claims description 3
• 230000001506 immunosuppresive effect Effects 0.000 claims description 3
• 208000004296 neuralgia Diseases 0.000 claims description 3
• 208000021722 neuropathic pain Diseases 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
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• 125000005544 phthalimido group Chemical group 0.000 claims description 3
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• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
• 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 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• 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 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 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 2
• FAJYEYOAVFDHOL-UHFFFAOYSA-N 5-(3-bromophenyl)-6-cyclohexyl-7-[6-(dimethylamino)pyridin-3-yl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(N(C)C)=CC=C1C1=NC2=NC=NC(N)=C2C(C=2C=C(Br)C=CC=2)=C1C1CCCCC1 FAJYEYOAVFDHOL-UHFFFAOYSA-N 0.000 claims description 2
• KGSUFXHWCXAXIT-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)-6-phenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1C=1C(C=2C=C(Br)C=CC=2)=C2C(N)=NC=NC2=NC=1C(C=N1)=CC=C1N1CCOCC1 KGSUFXHWCXAXIT-UHFFFAOYSA-N 0.000 claims description 2
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• DVCLZJGAKAKPRP-UHFFFAOYSA-N 6-benzyl-7-(6-morpholin-4-ylpyridin-3-yl)-5-phenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1C1=C2C(N)=NC=NC2=NC(C=2C=NC(=CC=2)N2CCOCC2)=C1CC1=CC=CC=C1 DVCLZJGAKAKPRP-UHFFFAOYSA-N 0.000 claims description 2
• FEEKONKMRMOMER-UHFFFAOYSA-N 7-(6-morpholin-4-ylpyridin-3-yl)-5,6-diphenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1C=1C(C=2C=CC=CC=2)=C2C(N)=NC=NC2=NC=1C(C=N1)=CC=C1N1CCOCC1 FEEKONKMRMOMER-UHFFFAOYSA-N 0.000 claims description 2
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