PT2670752E - Piperidinamidas pirrolopirazina-espirocíclicas como moduladores de canais iónicos - Google Patents

Info

Publication number

PT2670752E

PT2670752E PT127049856T PT12704985T PT2670752E PT 2670752 E PT2670752 E PT 2670752E PT 127049856 T PT127049856 T PT 127049856T PT 12704985 T PT12704985 T PT 12704985T PT 2670752 E PT2670752 E PT 2670752E

Authority

PT

Portugal

Prior art keywords

pain

mmol

compound

och

alkyl

Prior art date

2011-02-02

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• -1 piperidine amides Chemical class 0.000 title claims description 90
• 102000004310 Ion Channels Human genes 0.000 title description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 178
• 208000002193 Pain Diseases 0.000 claims description 135
• 230000036407 pain Effects 0.000 claims description 105
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 51
• 229910052717 sulfur Inorganic materials 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 125000004122 cyclic group Chemical group 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 34
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 31
• 208000004296 neuralgia Diseases 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 230000001154 acute effect Effects 0.000 claims description 18
• 206010019233 Headaches Diseases 0.000 claims description 17
• 208000021722 neuropathic pain Diseases 0.000 claims description 17
• 201000006417 multiple sclerosis Diseases 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 208000008035 Back Pain Diseases 0.000 claims description 12
• 206010003119 arrhythmia Diseases 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 231100000869 headache Toxicity 0.000 claims description 12
• 206010065390 Inflammatory pain Diseases 0.000 claims description 11
• 208000019695 Migraine disease Diseases 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 206010027599 migraine Diseases 0.000 claims description 11
• 208000000094 Chronic Pain Diseases 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
• 206010021639 Incontinence Diseases 0.000 claims description 9
• 206010028836 Neck pain Diseases 0.000 claims description 9
• 208000004550 Postoperative Pain Diseases 0.000 claims description 9
• 206010015037 epilepsy Diseases 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
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• 230000006793 arrhythmia Effects 0.000 claims description 7
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• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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• 208000020016 psychiatric disease Diseases 0.000 claims description 6
• 206010044652 trigeminal neuralgia Diseases 0.000 claims description 6
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
• 206010002383 Angina Pectoris Diseases 0.000 claims description 5
• 208000000003 Breakthrough pain Diseases 0.000 claims description 5
• 208000008765 Sciatica Diseases 0.000 claims description 5
• 230000002159 abnormal effect Effects 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 5
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• 208000020925 Bipolar disease Diseases 0.000 claims description 3
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 3
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
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• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 230000009529 traumatic brain injury Effects 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
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• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
• 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 claims 2
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• 101001032455 Dianthus caryophyllus Glutathione S-transferase 1 Proteins 0.000 claims 1
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• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
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• 230000001016 myotrophic effect Effects 0.000 claims 1
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• 239000000203 mixture Substances 0.000 description 185
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 106
• 235000019439 ethyl acetate Nutrition 0.000 description 105
• 239000000243 solution Substances 0.000 description 93
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 90
• 230000014759 maintenance of location Effects 0.000 description 89
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 87
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• 238000003556 assay Methods 0.000 description 83
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 76
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 239000012044 organic layer Substances 0.000 description 74
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• 239000007787 solid Substances 0.000 description 67
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
• AQTFKGDWFRRIHR-UHFFFAOYSA-L 3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoate;cobalt(2+);hydron Chemical compound [Co+2].[N-]1C(C=C2C(=C(C)C(C=C3C(=C(C)C(=C4)[N-]3)C=C)=N2)C=C)=C(C)C(CCC(O)=O)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 AQTFKGDWFRRIHR-UHFFFAOYSA-L 0.000 description 61
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
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• 238000000034 method Methods 0.000 description 45
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
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