BG105411A - 4,4-биарилпиперидинови производни с опиоидна рецепторна активност - Google Patents

Info

Publication number

BG105411A

BG105411A BG105411A BG10541101A BG105411A BG 105411 A BG105411 A BG 105411A BG 105411 A BG105411 A BG 105411A BG 10541101 A BG10541101 A BG 10541101A BG 105411 A BG105411 A BG 105411A

Authority

BG

Bulgaria

Prior art keywords

alkyl

phenyl

disorders

formula

piperidin

Prior art date

1998-09-09

Links

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• 102000003840 Opioid Receptors Human genes 0.000 title claims description 18
• 108090000137 Opioid Receptors Proteins 0.000 title claims description 18
• 230000000694 effects Effects 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 112
• 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• -1 phenyl naphthyl Chemical group 0.000 claims description 60
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
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• 208000035475 disorder Diseases 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 26
• 208000002193 Pain Diseases 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• 206010012335 Dependence Diseases 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 230000027455 binding Effects 0.000 claims description 12
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
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• AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 8
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• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 7
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• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
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• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 7
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 5
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• 229910052794 bromium Inorganic materials 0.000 claims description 5
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• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000011630 iodine Substances 0.000 claims description 5
• 231100001223 noncarcinogenic Toxicity 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 230000007547 defect Effects 0.000 claims description 4
• 230000006735 deficit Effects 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 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
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 3
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 208000023504 respiratory system disease Diseases 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 208000014674 injury Diseases 0.000 claims description 2
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
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• 239000000243 solution Substances 0.000 description 45
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