RU2549551C2 - Производные диазагомоадамантана и способы их применения - Google Patents

Info

Publication number

RU2549551C2

RU2549551C2 RU2012101784/04A RU2012101784A RU2549551C2 RU 2549551 C2 RU2549551 C2 RU 2549551C2 RU 2012101784/04 A RU2012101784/04 A RU 2012101784/04A RU 2012101784 A RU2012101784 A RU 2012101784A RU 2549551 C2 RU2549551 C2 RU 2549551C2

Authority

RU

Russia

Prior art keywords

diazatricyclo

undecane

pyridin

pain

alkyl

Prior art date

2009-06-19

Links

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• 238000000034 method Methods 0.000 title claims abstract description 270
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• 125000000217 alkyl group Chemical group 0.000 claims abstract description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
• 239000001257 hydrogen Substances 0.000 claims abstract description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 50
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 46
• 150000002367 halogens Chemical class 0.000 claims abstract description 46
• 239000012634 fragment Substances 0.000 claims abstract description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 37
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 37
• 230000000694 effects Effects 0.000 claims abstract description 36
• 125000003118 aryl group Chemical group 0.000 claims abstract description 33
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• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 614
• -1 1,3-thiazolyl Chemical group 0.000 claims description 332
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 100
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 93
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• 230000036407 pain Effects 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 28
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
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• 150000001408 amides Chemical class 0.000 claims description 15
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• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
• 210000003169 central nervous system Anatomy 0.000 claims description 12
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 125000001041 indolyl group Chemical group 0.000 claims description 11
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• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 9
• 229960004373 acetylcholine Drugs 0.000 claims description 9
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 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
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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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• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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• 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
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• 125000001624 naphthyl group Chemical group 0.000 claims description 6
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• 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
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• 208000008765 Sciatica Diseases 0.000 claims description 5
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
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• 206010053552 allodynia Diseases 0.000 claims description 5
• 238000011161 development Methods 0.000 claims description 5
• 230000009610 hypersensitivity Effects 0.000 claims description 5
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• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 5
• 230000005586 smoking cessation Effects 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
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• 230000003247 decreasing effect Effects 0.000 claims description 4
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• 230000009529 traumatic brain injury Effects 0.000 claims description 4
• 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
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• 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
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• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 3
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