KR20120044978A - 디아자호모아다만탄 유도체 및 이들의 사용 방법 - Google Patents

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Publication number

KR20120044978A

KR20120044978A KR1020127001339A KR20127001339A KR20120044978A KR 20120044978 A KR20120044978 A KR 20120044978A KR 1020127001339 A KR1020127001339 A KR 1020127001339A KR 20127001339 A KR20127001339 A KR 20127001339A KR 20120044978 A KR20120044978 A KR 20120044978A

Authority

KR

South Korea

Prior art keywords

undecane

diazacyclocyclo

pyridin

alkyl

haloalkyl

Prior art date

2009-06-19

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.)

Withdrawn

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• 238000000034 method Methods 0.000 title claims abstract description 147
• 150000001875 compounds Chemical class 0.000 claims abstract description 339
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 606
• -1 1,3-thiazolyl Chemical group 0.000 claims description 298
• 125000000217 alkyl group Chemical group 0.000 claims description 130
• 125000001188 haloalkyl group Chemical group 0.000 claims description 106
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 85
• 229910052739 hydrogen Inorganic materials 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 70
• 208000002193 Pain Diseases 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 55
• 230000036407 pain Effects 0.000 claims description 52
• 150000002431 hydrogen Chemical group 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 43
• 150000002367 halogens Chemical group 0.000 claims description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 29
• 208000004296 neuralgia Diseases 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 206010012289 Dementia Diseases 0.000 claims description 20
• 239000000651 prodrug Substances 0.000 claims description 20
• 229940002612 prodrug Drugs 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 201000000980 schizophrenia Diseases 0.000 claims description 19
• 208000024827 Alzheimer disease Diseases 0.000 claims description 18
• LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims description 18
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 208000021722 neuropathic pain Diseases 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 13
• 208000001294 Nociceptive Pain Diseases 0.000 claims description 13
• 150000001408 amides Chemical class 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 11
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 11
• 125000001041 indolyl group Chemical group 0.000 claims description 11
• 201000001119 neuropathy Diseases 0.000 claims description 11
• 230000007823 neuropathy Effects 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 208000005298 acute pain Diseases 0.000 claims description 10
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 208000004454 Hyperalgesia Diseases 0.000 claims description 9
• 230000007812 deficiency Effects 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 9
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
• 206010019233 Headaches Diseases 0.000 claims description 8
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• 239000003693 atypical antipsychotic agent Substances 0.000 claims description 8
• 229940127236 atypical antipsychotics Drugs 0.000 claims description 8
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• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
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• 230000007278 cognition impairment Effects 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 231100000869 headache Toxicity 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 206010027599 migraine Diseases 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 208000030507 AIDS Diseases 0.000 claims description 6
• 208000008035 Back Pain Diseases 0.000 claims description 6
• 206010058019 Cancer Pain Diseases 0.000 claims description 6
• 206010065390 Inflammatory pain Diseases 0.000 claims description 6
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• 206010029240 Neuritis Diseases 0.000 claims description 6
• 208000004550 Postoperative Pain Diseases 0.000 claims description 6
• 230000004064 dysfunction Effects 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 230000008764 nerve damage Effects 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
• 208000005171 Dysmenorrhea Diseases 0.000 claims description 5
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 5
• 208000001640 Fibromyalgia Diseases 0.000 claims description 5
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• 208000000450 Pelvic Pain Diseases 0.000 claims description 5
• 208000008765 Sciatica Diseases 0.000 claims description 5
• 206010039966 Senile dementia Diseases 0.000 claims description 5
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
• 208000016620 Tourette disease Diseases 0.000 claims description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 206010053552 allodynia Diseases 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 230000009610 hypersensitivity Effects 0.000 claims description 5
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 5
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 5
• 208000004371 toothache Diseases 0.000 claims description 5
• 230000009529 traumatic brain injury Effects 0.000 claims description 5
• WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 claims description 5
• 208000009935 visceral pain Diseases 0.000 claims description 5
• 201000010374 Down Syndrome Diseases 0.000 claims description 4
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 210000004558 lewy body Anatomy 0.000 claims description 4
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• UFDSVRIDRGHVGO-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 UFDSVRIDRGHVGO-UHFFFAOYSA-N 0.000 claims description 3
• HDNGCJMRFKVVBA-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 HDNGCJMRFKVVBA-UHFFFAOYSA-N 0.000 claims description 3
• XRSVWIJDRKTJFX-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-[4-(dimethylamino)phenyl]ethanone Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)N1C(CN(C2)C3)CC2CC3C1 XRSVWIJDRKTJFX-UHFFFAOYSA-N 0.000 claims description 3
• BSHJNFRDMXVCBN-UHFFFAOYSA-N 1-{2-[5-(1,4-diazatricyclo[4.3.1.13,8]undec-4-yl)pyridin-3-yl]phenyl}ethanone Chemical compound CC(=O)C1=CC=CC=C1C1=CN=CC(N2C3CC4CC(CN(C4)C3)C2)=C1 BSHJNFRDMXVCBN-UHFFFAOYSA-N 0.000 claims description 3
• 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims description 3
• KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
• 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 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• TWPWFUABIMXXNA-UHFFFAOYSA-N 3-(1,4-diazatricyclo[4.3.1.13,8]undecane-4-carbonyl)benzonitrile Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CC(C#N)=C1 TWPWFUABIMXXNA-UHFFFAOYSA-N 0.000 claims description 3
• RJBVGJISFOPTFT-UHFFFAOYSA-N 3-[5-(1,4-diazatricyclo[4.3.1.13,8]undec-4-yl)pyridin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(C=NC=2)N2C3CC4CC(CN(C4)C3)C2)=C1 RJBVGJISFOPTFT-UHFFFAOYSA-N 0.000 claims description 3
• ZJNLAVSXJIKECX-UHFFFAOYSA-N 4-[5-(1,4-diazatricyclo[4.3.1.13,8]undec-4-yl)pyridin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=CC(N2C3CC4CC(CN(C4)C3)C2)=C1 ZJNLAVSXJIKECX-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• QMKNDDIPPJRAOJ-UHFFFAOYSA-N N-[3-(1,4-diazatricyclo[4.3.1.13,8]undecane-4-carbonyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 QMKNDDIPPJRAOJ-UHFFFAOYSA-N 0.000 claims description 3
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