HU228314B1 - Kemokin receptor antagonisták, alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények - Google Patents

Info

Publication number

HU228314B1

HU228314B1 HU0500079A HUP0500079A HU228314B1 HU 228314 B1 HU228314 B1 HU 228314B1 HU 0500079 A HU0500079 A HU 0500079A HU P0500079 A HUP0500079 A HU P0500079A HU 228314 B1 HU228314 B1 HU 228314B1

Authority

HU

Hungary

Prior art keywords

group

substituted

aliphatic

aromatic

nmr

Prior art date

1998-09-04

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
• 239000002559 chemokine receptor antagonist Substances 0.000 title description 8
• 229940122444 Chemokine receptor antagonist Drugs 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 483
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 262
• -1 phospho, substituted benzyl Chemical group 0.000 claims description 226
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 182
• 125000001931 aliphatic group Chemical group 0.000 claims description 158
• 125000003118 aryl group Chemical group 0.000 claims description 121
• 229910052739 hydrogen Inorganic materials 0.000 claims description 65
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 49
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 46
• 238000002360 preparation method Methods 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 125000002252 acyl group Chemical group 0.000 claims description 15
• 238000011282 treatment Methods 0.000 claims description 15
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
• 230000002159 abnormal effect Effects 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 238000009825 accumulation Methods 0.000 claims description 11
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• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
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• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
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• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
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• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
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• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
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• 239000001301 oxygen Chemical group 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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• 229940079593 drug Drugs 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 239000011593 sulfur Chemical group 0.000 claims description 4
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
• 206010020751 Hypersensitivity Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 210000004698 lymphocyte Anatomy 0.000 claims description 2
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 claims 2
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 125000003431 oxalo group Chemical group 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
• 208000002874 Acne Vulgaris Diseases 0.000 claims 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical group CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
• 239000004593 Epoxy Chemical group 0.000 claims 1
• 206010063837 Reperfusion injury Diseases 0.000 claims 1
• 241000538730 Rocio Species 0.000 claims 1
• 208000034189 Sclerosis Diseases 0.000 claims 1
• 208000025865 Ulcer Diseases 0.000 claims 1
• 206010000496 acne Diseases 0.000 claims 1
• 210000000481 breast Anatomy 0.000 claims 1
• 244000309466 calf Species 0.000 claims 1
• 230000035622 drinking Effects 0.000 claims 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
• 208000037906 ischaemic injury Diseases 0.000 claims 1
• 230000000302 ischemic effect Effects 0.000 claims 1
• 230000003902 lesion Effects 0.000 claims 1
• 230000000527 lymphocytic effect Effects 0.000 claims 1
• 235000013372 meat Nutrition 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 462
• 238000005160 1H NMR spectroscopy Methods 0.000 description 256
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 228
• 239000000243 solution Substances 0.000 description 223
• 239000000047 product Substances 0.000 description 205
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 197
• 235000019439 ethyl acetate Nutrition 0.000 description 157
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 154
• 239000011541 reaction mixture Substances 0.000 description 135
• 239000000203 mixture Substances 0.000 description 131
• 238000005481 NMR spectroscopy Methods 0.000 description 109
• 239000002904 solvent Substances 0.000 description 107
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 95
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
• 230000002829 reductive effect Effects 0.000 description 80
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 77
• 235000019341 magnesium sulphate Nutrition 0.000 description 77
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
• 238000000034 method Methods 0.000 description 71
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 69
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• 229920006395 saturated elastomer Polymers 0.000 description 64
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 62
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• 239000012074 organic phase Substances 0.000 description 58
• 238000006243 chemical reaction Methods 0.000 description 53
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 51
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 47
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
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• 238000003756 stirring Methods 0.000 description 35
• 239000011780 sodium chloride Substances 0.000 description 34
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 31
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• 229940073584 methylene chloride Drugs 0.000 description 30
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
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