HUP0303107A2 - Gyulladásos betegségek kezelésére alkalmazható vegyületek, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények - Google Patents

Info

Publication number

HUP0303107A2

HUP0303107A2 HU0303107A HUP0303107A HUP0303107A2 HU P0303107 A2 HUP0303107 A2 HU P0303107A2 HU 0303107 A HU0303107 A HU 0303107A HU P0303107 A HUP0303107 A HU P0303107A HU P0303107 A2 HUP0303107 A2 HU P0303107A2

Authority

HU

Hungary

Prior art keywords

group

alkyl

aryl

formula

heteroaryl

Prior art date

2000-09-29

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 296
• 238000000034 method Methods 0.000 title claims description 45
• 238000002360 preparation method Methods 0.000 title claims description 23
• 230000008569 process Effects 0.000 title claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
• 208000027866 inflammatory disease Diseases 0.000 title claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 56
• 125000003118 aryl group Chemical group 0.000 claims abstract description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 46
• 239000001257 hydrogen Substances 0.000 claims abstract description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 7
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 60
• -1 {[({[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-amino)carbonyl]-amino}-methyl Chemical group 0.000 claims description 60
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
• 239000011593 sulfur Substances 0.000 claims description 17
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• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
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• 125000003277 amino group Chemical group 0.000 claims description 6
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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• 125000006277 halobenzyl group Chemical group 0.000 claims description 2
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• 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 2
• 230000002829 reductive effect Effects 0.000 claims description 2
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• 125000003342 alkenyl group Chemical group 0.000 abstract 3
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• 125000005018 aryl alkenyl group Chemical group 0.000 abstract 1
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 221
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• 239000000543 intermediate Substances 0.000 description 158
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• 239000000243 solution Substances 0.000 description 78
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• 239000000203 mixture Substances 0.000 description 70
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• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 37
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 33
• 229910021529 ammonia Inorganic materials 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
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• 238000003756 stirring Methods 0.000 description 24
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