TW200538460A - Phenylaminopropanol derivatives and methods of their use - Google Patents

Info

Publication number

TW200538460A

TW200538460A TW094109686A TW94109686A TW200538460A TW 200538460 A TW200538460 A TW 200538460A TW 094109686 A TW094109686 A TW 094109686A TW 94109686 A TW94109686 A TW 94109686A TW 200538460 A TW200538460 A TW 200538460A

Authority

TW

Taiwan

Prior art keywords

pain

methylamino

dihydro

patent application

scope

Prior art date

2004-03-30

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 86
• WXMQDCRVBPMUBV-UHFFFAOYSA-N 1-anilinopropan-1-ol Chemical class CCC(O)NC1=CC=CC=C1 WXMQDCRVBPMUBV-UHFFFAOYSA-N 0.000 title abstract description 5
• 208000002193 Pain Diseases 0.000 claims abstract description 115
• 230000036407 pain Effects 0.000 claims abstract description 100
• 239000000203 mixture Substances 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
• 208000024891 symptom Diseases 0.000 claims abstract description 43
• 208000035475 disorder Diseases 0.000 claims abstract description 33
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 23
• 230000002496 gastric effect Effects 0.000 claims abstract description 12
• 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims abstract description 11
• 208000024714 major depressive disease Diseases 0.000 claims abstract description 11
• 230000000407 monoamine reuptake Effects 0.000 claims abstract description 11
• 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims abstract description 11
• 230000001457 vasomotor Effects 0.000 claims abstract description 11
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims description 176
• -1 phenyl fluorenyl Chemical group 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 30
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 241000282414 Homo sapiens Species 0.000 claims description 17
• 230000002792 vascular Effects 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
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• 230000001568 sexual effect Effects 0.000 claims description 13
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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• 230000002093 peripheral effect Effects 0.000 claims description 12
• 229910052720 vanadium Inorganic materials 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 230000009245 menopause Effects 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 206010021639 Incontinence Diseases 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 208000009935 visceral pain Diseases 0.000 claims description 10
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 208000014674 injury Diseases 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
• 206010064012 Central pain syndrome Diseases 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 230000004899 motility Effects 0.000 claims description 8
• 150000002825 nitriles Chemical class 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 230000001684 chronic effect Effects 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 208000002720 Malnutrition Diseases 0.000 claims description 6
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 6
• 125000001118 alkylidene group Chemical group 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 238000001356 surgical procedure Methods 0.000 claims description 6
• 206010058019 Cancer Pain Diseases 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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• 125000004104 aryloxy group Chemical group 0.000 claims description 5
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• WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
• 210000005036 nerve Anatomy 0.000 claims description 5
• 210000000056 organ Anatomy 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
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• 206010005052 Bladder irritation Diseases 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 208000025865 Ulcer Diseases 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
• 125000006622 cycloheptylmethyl group Chemical group 0.000 claims description 4
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 201000000736 Amenorrhea Diseases 0.000 claims description 3
• 206010001928 Amenorrhoea Diseases 0.000 claims description 3
• 208000006820 Arthralgia Diseases 0.000 claims description 3
• 208000035143 Bacterial infection Diseases 0.000 claims description 3
• 208000017283 Bile Duct disease Diseases 0.000 claims description 3
• 206010006002 Bone pain Diseases 0.000 claims description 3
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• 208000004232 Enteritis Diseases 0.000 claims description 3
• 208000007882 Gastritis Diseases 0.000 claims description 3
• 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 claims description 3
• 208000025966 Neurological disease Diseases 0.000 claims description 3
• 208000001294 Nociceptive Pain Diseases 0.000 claims description 3
• 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
• 208000036142 Viral infection Diseases 0.000 claims description 3
• 125000004423 acyloxy group Chemical group 0.000 claims description 3
• 231100000540 amenorrhea Toxicity 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 201000005442 glossopharyngeal neuralgia Diseases 0.000 claims description 3
• 230000008595 infiltration Effects 0.000 claims description 3
• 238000001764 infiltration Methods 0.000 claims description 3
• 235000000824 malnutrition Nutrition 0.000 claims description 3
• 230000001071 malnutrition Effects 0.000 claims description 3
• 235000018343 nutrient deficiency Nutrition 0.000 claims description 3
• 208000015380 nutritional deficiency disease Diseases 0.000 claims description 3
• 230000011514 reflex Effects 0.000 claims description 3
• 208000019116 sleep disease Diseases 0.000 claims description 3
• 210000004872 soft tissue Anatomy 0.000 claims description 3
• 230000002889 sympathetic effect Effects 0.000 claims description 3
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• 239000003053 toxin Substances 0.000 claims description 3
• 231100000765 toxin Toxicity 0.000 claims description 3
• 108700012359 toxins Proteins 0.000 claims description 3
• 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 208000011231 Crohn disease Diseases 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 208000008930 Low Back Pain Diseases 0.000 claims description 2
• 208000028389 Nerve injury Diseases 0.000 claims description 2
• 206010041250 Social phobia Diseases 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 206010012601 diabetes mellitus Diseases 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
• 230000008764 nerve damage Effects 0.000 claims description 2
• 230000035946 sexual desire Effects 0.000 claims description 2
• 208000022925 sleep disturbance Diseases 0.000 claims description 2
• 210000000273 spinal nerve root Anatomy 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical group 0.000 claims description 2
• 230000008736 traumatic injury Effects 0.000 claims description 2
• ZTUMICIIVZMNFY-UHFFFAOYSA-N 1-(methylamino)-1-phenylpropan-2-ol Chemical compound CNC(C(C)O)C1=CC=CC=C1 ZTUMICIIVZMNFY-UHFFFAOYSA-N 0.000 claims 1
• PUFWGUZSDHANBX-UHFFFAOYSA-N 1-phenyl-9h-fluorene Chemical compound C=12CC3=CC=CC=C3C2=CC=CC=1C1=CC=CC=C1 PUFWGUZSDHANBX-UHFFFAOYSA-N 0.000 claims 1
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
• 206010065016 Post-traumatic pain Diseases 0.000 claims 1
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
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• 230000001668 ameliorated effect Effects 0.000 abstract 1
• 231100000872 sexual dysfunction Toxicity 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
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