BG64556B1 - Кондензирани с арил азаполициклични съединения - Google Patents

Info

Publication number

BG64556B1

BG64556B1 BG104983A BG10498300A BG64556B1 BG 64556 B1 BG64556 B1 BG 64556B1 BG 104983 A BG104983 A BG 104983A BG 10498300 A BG10498300 A BG 10498300A BG 64556 B1 BG64556 B1 BG 64556B1

Authority

BG

Bulgaria

Prior art keywords

triene

trideca

alkyl

tetraene

hexadeca

Prior art date

1998-04-29

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 289
• 125000003118 aryl group Chemical group 0.000 title claims description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 48
• -1 hydroxy, nitro, amino Chemical group 0.000 claims description 46
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 229920006395 saturated elastomer Polymers 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 26
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 229960002715 nicotine Drugs 0.000 claims description 14
• 230000009529 traumatic brain injury Effects 0.000 claims description 14
• 208000018737 Parkinson disease Diseases 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 12
• 208000010877 cognitive disease Diseases 0.000 claims description 12
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 125000005605 benzo group Chemical group 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 229910052717 sulfur Chemical group 0.000 claims description 11
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 9
• 208000023105 Huntington disease Diseases 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
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• 208000035475 disorder Diseases 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
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• 239000000126 substance Substances 0.000 claims description 7
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000001246 bromo group Chemical group Br* 0.000 claims description 6
• 230000026781 habituation Effects 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 150000005672 tetraenes Chemical class 0.000 claims description 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
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• 229910052799 carbon Inorganic materials 0.000 claims description 5
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• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 231100000869 headache Toxicity 0.000 claims description 5
• 125000002346 iodo group Chemical group I* 0.000 claims description 5
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• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
• 231100000397 ulcer Toxicity 0.000 claims description 5
• 230000025033 vasoconstriction Effects 0.000 claims description 5
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
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• 208000020925 Bipolar disease Diseases 0.000 claims description 4
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• 206010012289 Dementia Diseases 0.000 claims description 4
• 208000012661 Dyskinesia Diseases 0.000 claims description 4
• 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
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• 239000011737 fluorine Substances 0.000 claims description 4
• 230000000968 intestinal effect Effects 0.000 claims description 4
• 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• MNOULQLXILYKNV-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CC=NN1 MNOULQLXILYKNV-UHFFFAOYSA-N 0.000 claims description 3
• 208000015943 Coeliac disease Diseases 0.000 claims description 3
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
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• 208000003443 Unconsciousness Diseases 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 208000028591 pheochromocytoma Diseases 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 2
• 230000019771 cognition Effects 0.000 claims description 2
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• 150000003457 sulfones Chemical class 0.000 claims description 2
• 150000003462 sulfoxides Chemical class 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 241000208125 Nicotiana Species 0.000 claims 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
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• 230000006793 arrhythmia Effects 0.000 claims 1
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• 208000013403 hyperactivity Diseases 0.000 claims 1
• IGRXMNYYQGKFCK-UHFFFAOYSA-N trideca-2,4,6-triene Chemical compound CCCCCCC=CC=CC=CC IGRXMNYYQGKFCK-UHFFFAOYSA-N 0.000 claims 1
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 148
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• 239000000203 mixture Substances 0.000 description 72
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 58
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
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